Hydrochloric Acid → 1-(2-Amino-acetyl)-pyrrolidine-2-carbonitrile hydrochloride

HRID 1925076Notes

Reaction equation

HRID 1925076 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]#[N:17])=[O:10])(C)(C)C.[ClH:19]>CCOCC.O>[ClH:19].[NH2:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]#[N:17])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67519316(S)-tert-butyl 2-(2-cyanopyrrolidin-1-yl)-2-oxoethylcarbamate

Product 1

HCID 689101291-(2-Amino-acetyl)-pyrrolidine-2-carbonitrile hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 1e (13.7 g, 54.2 mmol) was dissolved in the solvent mixture of 140 mL of ether and 40 mL of water, and 37% hydrochloride acid (90 mL) were then added dropwise to the solution. Upon completion of the addition, the reaction mixture was stirred for 1 hour in an ice-water bath, the solvent was evaporated, and ether was added to the residue to centrifuge to give 1-(2-amino-acetyl)-pyrrolidine-2-carbonitrile hydrochloride 1d (10 g, yield 98%) as a white powder.

Workup

  1. additionwere then added dropwise to the solution
  2. additionUpon completion of the addition
  3. customthe solvent was evaporated
  4. additionether was added to the residue to centrifuge

Sources & evidence

ORD record
ord-79342eee9f15499d8490f2c4e699e842
Source dataset
uspto-grants-2012_05
Patent number
US08178575B2

Reaction notes

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