Benzyl chloroformate → Cbz-L-Prolinol

HRID 2399900Notes

Reaction equation

HRID 2399900 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[OH-].[Na+]>C(OCC)C>[C:13]1([CH2:12][O:11][C:9]([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][OH:7])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 640091L-Prolinol

Product 1

HCID 11096562Cbz-L-ProlinolYield 101.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 25 g of (S)-2-pyrrolidinemethanol in 150 ml of diethyl ether is added 54.8 g of benzyl chloroformate. At mid point of addition, 49.4 ml of 5N sodium hydroxide is added, simultaneously, and the reaction stirred at 0° C. for 2 hours. Diethyl ether is added, the layers are separated and the aqueous layer reextracted with diethyl ether. The combined organic layers are dried, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel, 0-10% methyl alcohol/methylene chloride) to give 59.1 g of (S)-2-hydroxymethyl-1-pyrrolidine carboxylic acid phenylmethyl ester.

Workup

  1. additionis added
  2. customthe layers are separated
  3. customThe combined organic layers are dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography (silica gel, 0-10% methyl alcohol/methylene chloride)

Sources & evidence

ORD record
ord-5f60dbf50c11434d9c45818f4bf6c176
Source dataset
uspto-grants-1995_09
Patent number
US05451685

Reaction notes

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