Sodium Carbonate → (R)-(-)-1-CBZ-3-pyrrolidinol
Reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C1COCC1.O>[CH2:17]([O:16][C:14]([N:4]1[CH2:5][CH2:6][C@@H:2]([OH:1])[CH2:3]1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of (R)-3-hydroxypyrrolidine (4.35 g, 50 mmol) in THF (50 mL) and aqueous sodium carbonate (10.6 g, 100 mmol in 50 mL water) cooled to 0° C. was added a solution of benzyl chloroformate in THF (60 mmol, 8.6 mL in 10 mL THF) over a period of 5-10 min. After stirring at 0° C. for 2 h, the reaction mixture was diluted with 200 mL water and extracted with methylene chloride (3×100 mL). The combined extracts were washed with 1N sulfuric acid (3×75 mL) followed by brine solution (3×50 mL). This extract was then dried over anhydrous sodium sulfate and the solvent evaporated to give a light yellow oil (10.5 g, 95% yield) which was used for the next reaction without any purification.
Workup
- extractionextracted with methylene chloride (3×100 mL)
- washThe combined extracts were washed with 1N sulfuric acid (3×75 mL)
- dry with materialThis extract was then dried over anhydrous sodium sulfate
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-d954c25548384bed9a76118cfa2de305
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06649642B2
Reaction notes
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