(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate
- Product Name
- (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate
- CAS No.
- 635319-09-4
- Chemical Name
- (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate
- Synonyms
- tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate;(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate;1,1-Dimethylethyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-pyrrolidinecarboxylate;1-Pyrrolidinecarboxylic acid, 3-hydroxy-4-(hydroxymethyl)-, 1,1-dimethylethyl ester, (3R,4R)-
- CBNumber
- CB12694480
- Molecular Formula
- C10H19NO4
- Formula Weight
- 217.26
- MOL File
- 635319-09-4.mol
(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate Property
- Boiling point:
- 340.3±27.0 °C(Predicted)
- Density
- 1.190±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 14.49±0.40(Predicted)
- Appearance
- Light yellow to brown Solid
- optical activity
- 15°(C=0.01g/ml MEOH)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- B692210
- Product name
- (3R,4R)-tert-Butyl3-Hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
- Packaging
- 500mg
- Price
- $1320
- Updated
- 2021/12/16
- Product number
- 63410
- Product name
- (3R,4R)-tert-Butyl3-Hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
- Packaging
- 50mg
- Price
- $650
- Updated
- 2021/12/16
- Product number
- 63410
- Product name
- (3R,4R)-tert-Butyl3-Hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
- Packaging
- 500mg
- Price
- $2200
- Updated
- 2021/12/16
- Product number
- CCH0065810
- Product name
- TERT-BUTYL-(3R,4R)-3-HYDROXY-4-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $459.61
- Updated
- 2021/12/16
- Product number
- CD11082862
- Product name
- (3R,4R)-tert-Butyl3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
- Purity
- 95+%
- Packaging
- 1g
- Price
- $541
- Updated
- 2021/12/16
(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate Chemical Properties,Usage,Production
Uses
(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate has been used as a reactant for the preparation of transition state analogue inhibitors of human 5’-Methylthioadenosine phosphorylase (MTAP).
Synthesis
635319-08-3
635319-09-4
The general procedure for the synthesis of tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate from the compound (CAS: 635319-08-3) was as follows: to an ethanol ((S)-1,2-dihydroxyethyl)pyrrolidine (3.4 g, 13.7 mmol) solution of N-tert-butoxycarbonyl-(3R,4S)-3-hydroxy-4-[(S)-1,2-dihydroxyethyl]pyrrolidine ( 50 mL) solution of sodium periodate (3.4 g, 16 mmol) was added dropwise to an aqueous (25 mL) solution of sodium periodate (3.4 g, 16 mmol) while maintaining the reaction temperature at 0 °C. The reaction mixture was continued to be stirred at 0 °C for 20 min. Subsequently, sodium borohydride (2.0 g, excess) was added in batches to ensure that the reaction temperature was maintained at 0 °C. After completion of addition, the solids were removed by filtration and the filter cake was washed with ethanol (50 mL). The filtrates were combined and concentrated in vacuum to give a syrupy product. Purification by column chromatography gave the target product 1 (2.74 g, 92% yield) in syrupy form.
References
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 24, p. 5271 - 5276
[2] Patent: WO2004/18496, 2004, A1. Location in patent: Page 23-24
(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate Preparation Products And Raw materials
Raw materials
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