Hydrochloric Acid → (S)-2-(Pyrrolidin-2-yl)acetonitrile hydrochloride

HRID 928013Notes

Reaction equation

HRID 928013 reaction equation
[C:1]([CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)#[N:2].[ClH:16]>CO>[ClH:16].[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10727174tert-butyl (2S)-2-(cyanomethyl)pyrrolidine-1-carboxylate2×

Product 1

HCID 86713338(S)-2-(Pyrrolidin-2-yl)acetonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of tert-butyl (S)-2-cyanomethylpyrrolidine-1-carboxylate (Intermediate 139, 13.0 g) in methanol (130 mL) and concentrated hydrochloric acid (13 mL) was stirred and heated at 40° C. overnight. After cooling, the mixture was concentrated under vacuum and the residue was diluted with toluene and reconcentrated. Ethanol (20 mL) was added and the resultant solid was collected by filtration and washed with hexane to give ((S)-pyrrolidin-2-yl)acetonitrile hydrochloride (8.0 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under vacuum
  3. additionthe residue was diluted with toluene
  4. additionEthanol (20 mL) was added
  5. filtrationthe resultant solid was collected by filtration
  6. washwashed with hexane

Sources & evidence

ORD record
ord-b7812456ee8848e285e578d2e1c658e1
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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