Water → Cbz-D-prolinol

HRID 901971Notes

Reaction equation

HRID 901971 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][OH:7].O.C(=O)([O-])O.[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(OCC)(=O)C>[OH:7][CH2:6][C@H:2]1[CH2:3][CH2:4][CH2:5][N:1]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 2724541Prolinol, (R)-

Product 1

HCID 5314177Cbz-D-prolinol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2 g (0.0198 mol) of (2R)-pyrrolidin-2-ylmethanol was dissolved in 20 mL of ethyl acetate, 20 mL of water was added thereto, and the mixture was stirred. 3.3 g (0.30 mol) of sodium hydrogencarbonate was added to the mixture, followed by stirring of the mixture for 5 minutes. 4.24 mL (0.03 mol) of benzyl chloroformate was added dropwise to the mixture, followed by stirring for 5 hours. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to quantitatively obtain the title compound.

Workup

  1. stirringby stirring of the mixture for 5 minutes
  2. stirringby stirring for 5 hours
  3. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-75db90d82a3f47dc8b976ee7874f1654
Source dataset
uspto-grants-2008_04
Patent number
US07365067B2

Reaction notes

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