2,2,2-Trifluoroethanol → HCID 77699059, compound

HRID 1498977Notes

Reaction equation

HRID 1498977 reaction equation
F[C:2](F)(F)[CH2:3][OH:4].[N+:7]([CH2:10][CH:11]1[CH2:15][CH:14]([CH2:16][CH:17]=C)[C:13](=O)[CH2:12]1)([O-:9])=[O:8].[C:20]([O-:23])(=O)[CH3:21].[NH4+:24].[C:25]([N+:29]#[C-])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([NH:29][C:3]([C:2]1([NH:24][C:20]([CH3:21])=[O:23])[CH:13]([CH2:14][CH:16]=[CH2:17])[CH2:12][CH:11]([CH2:10][N+:7]([O-:9])=[O:8])[CH2:15]1)=[O:4])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 675151713-Nitromethyl-5-(propene-3-yl)cyclopentanone

Product 1

HCID 77699059HCID 77699059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring 2,2,2-trifluoroethanol (1.5 mL) solution of 3-nitromethyl-5-(propene-3-yl)cyclopentanone (mixture of isomers (0.366 g, 2.0 mmol)), under an inert atmosphere of nitrogen was added ammonium acetate (0.617 g, 8 mmol) and t-butylisonitrile (0.68 mL, 6.0 mmol) and the reaction mixture was stirred at room temperature for 2 days. The mixture was then diluted with methylene chloride (20 mL) and directly loaded onto a silica gel column (˜250 mL). The two cyclopentane-t-butyl carboxamide isomers with the acetamino and allyl substituents in syn conformation (isomers 1 and 2), elute first, followed by elution of isomer A (122 mg, 19%), and then isomer B (195 mg, 30%) as white solids.

Workup

  1. washThe two cyclopentane-t-butyl carboxamide isomers with the acetamino and allyl substituents in syn conformation (isomers 1 and 2), elute first
  2. washfollowed by elution of isomer A (122 mg, 19%)

Sources & evidence

ORD record
ord-81f2fb2c351b4e99819a335a777ed02f
Source dataset
uspto-grants-2015_12
Patent number
US09200011B2

Reaction notes

Loading…