tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate
- Product Name
- tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate
- CAS No.
- 1172623-99-2
- Chemical Name
- tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate
- Synonyms
- Omarigliptin Intermediate;(5S,6R)-5-(Boc-amino)-6-(2,5-difluorophenyl)-3-hydroxytetrahydropyran;tert-butyl N-[(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxyoxan-3-yl]carbamate;tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate;tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Synonyms;(2xi,5R)-1,5-Anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-pentitol;D-glycero-Pentitol, 1,5-anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2ξ,5R)-
- CBNumber
- CB42736769
- Molecular Formula
- C16H21F2NO4
- Formula Weight
- 329.34
- MOL File
- 1172623-99-2.mol
tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Property
- Boiling point:
- 439.7±45.0 °C(Predicted)
- Density
- 1.26±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Store in freezer, under -20°C
- pka
- 11.31±0.60(Predicted)
- Appearance
- Off-white to gray Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- CS-M3107
- Product name
- D-glycero-Pentitol,1,5-anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2ξ,5R)-
- Packaging
- 250mg
- Price
- $118
- Updated
- 2021/12/16
- Product number
- CS-M3107
- Product name
- D-glycero-Pentitol,1,5-anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2ξ,5R)-
- Packaging
- 1g
- Price
- $290
- Updated
- 2021/12/16
- Product number
- 6963EA
- Product name
- Tert-Butyl((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
- Packaging
- 5g
- Price
- $458
- Updated
- 2021/12/16
- Product number
- A604202
- Product name
- tert-Butyl((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
- Purity
- 95+%
- Packaging
- 100mg
- Price
- $55
- Updated
- 2021/12/16
- Product number
- A604202
- Product name
- tert-Butyl((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $88
- Updated
- 2021/12/16
tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Chemical Properties,Usage,Production
Synthesis
1172623-98-1
1172623-99-2
Tert-butyl ((2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl)carbamate (8.9 g, 28.6 mmol) was dissolved in anhydrous methyl tert-butyl ether (90 mL), anhydrous toluene (9 mL) was added, and the reaction system was cooled down to -10 °C. Tetrahydrofuran solution of borane dimethyl sulfide (2 mol/L, 35.9 mL) was added slowly, and the reaction temperature was maintained at 0°C for 3.5 hours. Upon completion of the reaction, water (4 mL) was slowly added followed by dropwise addition of sodium hydroxide solution (1 mol/L, 89 mL) and stirred for 15 minutes. Sodium perborate (13.2 g, 85.8 mmol) was added in batches and stirred overnight at room temperature. After completion of the reaction, the reaction solution was left to partition and the aqueous phase was extracted with methyl tert-butyl ether (50 mL x 2). The organic phases were combined, washed with saturated sodium chloride solution (20 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated. Toluene (50 mL) was added to the concentrate and heated to 90°C to dissolve. Slowly added n-hexane (200mL) dropwise to the reaction solution, precipitated white solid, filtered. The filter cake was washed with hexane (30 mL x 2) and concentrated to remove the solvent to give a white solid powder target product ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamic acid tert-butyl ester (7.9 g, 84% yield). Mass spectrum (ESI) m/z: 274.1 [M-55].
References
[1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1760 - 1768
[2] Patent: EP3159344, 2017, A1. Location in patent: Paragraph 0096; 0097; 0104
[3] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 33; 36
[4] Patent: TW2017/8224, 2017, A. Location in patent: Page/Page column 28; 32
[5] Patent: TW2017/8220, 2017, A. Location in patent: Page/Page column 56; 57; 60
tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Preparation Products And Raw materials
Raw materials
Preparation Products
tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Suppliers
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View Lastest Price from tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate manufacturers
- Product
- tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate Synonyms 1172623-99-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200kg
- Release date
- 2019-12-20