tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Product Name
- tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- CAS No.
- 622867-52-1
- Chemical Name
- tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Synonyms
- 2-Boc-6-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline;tert-butyl 6-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate;tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate;6-Hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-6-(hydroxymethyl)-, 1,1-dimethylethyl ester
- CBNumber
- CB33060635
- Molecular Formula
- C15H21NO3
- Formula Weight
- 263.33
- MOL File
- 622867-52-1.mol
tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate Property
- Boiling point:
- 403.7±45.0 °C(Predicted)
- Density
- 1.153±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 14.44±0.10(Predicted)
- Appearance
- White to off-white Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
N-Bromosuccinimide Price
- Product number
- B656550
- Product name
- N-Boc-6-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
- Packaging
- 250mg
- Price
- $220
- Updated
- 2021/12/16
- Product number
- P000526310
- Product name
- tert-Butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $259
- Updated
- 2021/12/16
- Product number
- 2029AQ
- Product name
- tert-butyl6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Packaging
- 250mg
- Price
- $414.8
- Updated
- 2021/12/16
- Product number
- P000526310
- Product name
- tert-Butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Purity
- 95+%
- Packaging
- 100mg
- Price
- $164
- Updated
- 2021/12/16
- Product number
- P000526310
- Product name
- tert-Butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
- Purity
- 95+%
- Packaging
- 1g
- Price
- $650
- Updated
- 2021/12/16
tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate Chemical Properties,Usage,Production
Uses
N-Boc-6-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline is an intermediate used to prepare phosphonate-substituted HIV protease inhibitors for treatment of AIDS and other viral infections. It is also used in the synthesis of immunosuppressant heterocyclic compdounds for treating or preventing diseases assocd. with EDG receptor mediated signal transduction.
Synthesis
170097-67-3
622867-52-1
General procedure for the synthesis of tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate from 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid: In Example 16, tert-butyl 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2- carboxylate (D-1 ), the intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid, was prepared as follows: firstly, under nitrogen protection, the Borane-THF complex (99.17 mL, 99.17 mmol) was slowly added to a solution of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (12.50 g, 45.08 mmol) in anhydrous THF (125.0 mL) via a syringe, and the reaction lasted for 16 h at 25 °C. Subsequently, water (10.0 mL) was slowly added followed by 2.0 M Na2CO3 solution (15.0 mL). The mixture was stirred for 15 min and then diluted with EtOAc to separate the organic layer. The organic layer was washed with 1 M HCl, dried over MgSO4 and concentrated under reduced pressure to give an oil. The oily substance was purified by silica gel chromatography to give the intermediate D-1-1 (11.8 g, 99.3% yield) as a white solid. Next, D-1-1 (9.50 g, 36.1 mmol) and N,N-diisopropylethylamine (9.43 mL, 54.1 mmol) were dissolved in dichloromethane (200.0 mL), triphenylphosphine dibromide (23.79 g, 54.11 mmol) was added, and the reaction was stirred for 1 hr and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford the target product D-1 (8.74 g, 74% yield) as a white solid.
References
[1] Patent: US2016/24059, 2016, A1. Location in patent: Paragraph 0308-0309
[2] Patent: WO2012/122340, 2012, A1. Location in patent: Page/Page column 77
[3] Patent: US2014/73629, 2014, A1. Location in patent: Paragraph 0100; 0101
[4] Patent: WO2017/160632, 2017, A1. Location in patent: Page/Page column 78; 79
[5] Patent: WO2017/216726, 2017, A1. Location in patent: Page/Page column 643-644
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