Trifluoroacetic acid → (1R,3R)-3-aminocyclopentane-1-carbonitrile 2,2,2-trifluoroacetate
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.