Chloroacetyl chloride → 2-Pyrrolidinemethanol, 1-(chloroacetyl)-, (2S)-

HRID 1982643Notes

Reaction equation

HRID 1982643 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH:6]1[CH2:12][CH2:11][CH2:10][C@H:7]1[CH2:8][OH:9].C([O-])(=O)C.[Na+]>CC(C)=O.O>[Cl:1][CH2:2][C:3]([N:6]1[CH2:12][CH2:11][CH2:10][C@H:7]1[CH2:8][OH:9])=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 640091L-Prolinol

Product 1

HCID 450807952-Pyrrolidinemethanol, 1-(chloroacetyl)-, (2S)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of chloroacetyl chloride, 27.7 g (0.247 mol), in 66.5 ml of acetone is added dropwise with stirring to a solution of 25 g (0.247 mol) of L-prolinol and 40.4 g (0.493 mol) of sodium acetate in a mixture of 400 ml of acetone and 200 ml of water at 0°-5° C. The mixture is stirred and allowed to reach room temperature over two hours, the solvent is evaporated in vacuo and the residue is suspended in 300 ml chloroform and washed with water, 2×300 ml. The chloroform layer is separated, dried over sodium sulfate, evaporated in vacuo and the residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (98:2) to give (S)-1-(chloroacetyl)-2-pyrrolidinemethanol, 34.1 g; [α]D25 -62.2° (c 1.00, methanol).

Workup

  1. customthe solvent is evaporated in vacuo
  2. washwashed with water, 2×300 ml
  3. customThe chloroform layer is separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue is purified by chromatography
  7. washeluting with dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-73ede2a65ca2402a92f2a83aaf63b821
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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