Chloroacetyl chloride → 1,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate

HRID 421183Notes

Reaction equation

HRID 421183 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:24][CH2:25][C:26]([NH:10][CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 592157991,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (1.34 ml, 7.5 mmol) was added to a solution of 1,1-dimethylethyl (2R)-2-(aminomethyl)-1-pyrrolidinecarboxylate (1 g, 5 mmol) in 50 ml of DCM; then chloroacetyl chloride (0.418 ml, 5.25 mmol) was slowly added and the reaction mixture stirred 1 h before being worked up. DCM was added and the organic phase was washed with a saturated solution of ammonium chloride. The crude was purified by flash chromatography eluting with cyclohexane/ethyl acetate 8/2 affording 1.28 g of the target material.

Workup

  1. washthe organic phase was washed with a saturated solution of ammonium chloride
  2. customThe crude was purified by flash chromatography
  3. washeluting with cyclohexane/ethyl acetate 8/2 affording 1.28 g of the target material

Sources & evidence

ORD record
ord-a7fc1115e89e483c92124b068770370d
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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