Trifluoroacetic acid → (cis-3-Amino-cyclopentyl)-acetonitrile trifluoroacetate

HRID 245917Notes

Reaction equation

HRID 245917 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][C:14]#[N:15])[CH2:9]1)(C)(C)C.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[NH2:7][C@@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][C:14]#[N:15])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20729728tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

Product 1

HCID 18453414(cis-3-Amino-cyclopentyl)-acetonitrile trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask, (cis-3-cyanomethyl-cyclopentyl)-carbamic acid tert-butyl ester (188 mg, 0.84 mmol) was dissolved in dichloromethane (5 ml) and trifluoroacetic acid (2.0 ml, 26.0 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 h then concentrated to afford (cis-3-amino-cyclopentyl)-acetonitrile trifluoroacetate as a yellow oil which was used without further purification.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-f774e9bc046b4c56937ec4610ff05dad
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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