Hydrochloric Acid → HCID 86648337, compound

HRID 1961569Notes

Reaction equation

HRID 1961569 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]#[N:17])=[O:10])(C)(C)C.O.[ClH:20]>CCOCC>[ClH:20].[NH2:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]#[N:17])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68036711HCID 68036711, compound

Product 1

HCID 86648337HCID 86648337, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(S)-[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 1c (13.7 g, 54.2 mmol) was dissolved in 140 mL of ether and 40 mL of water with stirring. Upon cooling by an ice-water bath, 37% hydrochloric acid (90 mL) was dropwise added and the reaction mixture was stirred for 1 hour at the same temperature. The mixture was concentrated under reduced pressure and the residue diluted with ether was filtered with a filtering centrifuge to obtain the title compound (S)-1-(2-amino-acetyl)-pyrrolidine-2-carbonitrile hydrochloride 1d (10 g, yield 98%) as a white powder.

Workup

  1. temperatureUpon cooling by an ice-water bath
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue diluted with ether
  4. filtrationwas filtered with a filtering centrifuge

Sources & evidence

ORD record
ord-015400e26b4346d59b78c73f1f5cc98a
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

Loading…