Trifluoroacetic acid → (1R,3R)-3-aminocyclopentane-1-carbonitrile 2,2,2-trifluoroacetate

HRID 245859Notes

Reaction equation

HRID 245859 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC(=O)[NH:14][C@@H:15]1[CH2:19][CH2:18][C@@H:17]([C:20]#[N:21])[CH2:16]1)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:14][C@@H:15]1[CH2:19][CH2:18][C@@H:17]([C:20]#[N:21])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279906tert-Butyl ((1R,3R)-3-cyanocyclopentyl)carbamate

Product 1

HCID 71280560(1R,3R)-3-aminocyclopentane-1-carbonitrile 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, ((1R,3R)-3-cyano-cyclopentyl)-carbamic acid tert-butyl ester (crude from Step 2) was dissolved in dichloromethane (2.5 ml). The solution was cooled to 0° C. and trifluoroacetic acid (1.1 ml, 14.3 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 h then concentrated to give (1R,3R)-3-amino-cyclopentanecarbonitrile trifluoroacetate as a light brown oil which was used without further purification.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. concentrationthen concentrated

Sources & evidence

ORD record
ord-75ace3c5740441a280663fadbc18f442
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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