2,2,2-Trifluoroethanol → HCID 69669543, compound

HRID 590690Notes

Reaction equation

HRID 590690 reaction equation
[CH2:1]([CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=O)[CH:2]=[CH2:3].[C:10]([O-:13])(=O)[CH3:11].[NH4+:14].[C:15]([N+:19]#[C-])([CH3:18])([CH3:17])[CH3:16].FC(F)(F)[CH2:23][OH:24]>ClCCl>[C:10]([NH:14][C@@:5]1([C:23]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:24])[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:1][CH:2]=[CH2:3])(=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 109205112-Allylcyclopentanone

Product 1

HCID 69669543HCID 69669543, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring mixture of 2-allylcyclopentanone (0.993 g, 8 mmol) and ammonium acetate (1.54 g, 20 mmol) in 2,2,2-trifluoroethanol (2.5 mL) was treated with t-butyl isocyanide (1.81 mL, 16 mmol). The reaction mixture was stirred at room temperature for 4 days, following which the mixture was dissolved in a minimum amount of dichloromethane and purified by flash column chromatography (silica gel, 60% ethyl acetate in heptane) to afford the anti-isomer of (1S,2S)-1-acetamido-2-allyl-N-tert-butylcyclopentane carboxamide (0.771 g, 36%) as a white solid. The later migrating syn-isomer is obtained as a white solid (0.851 g, 40%), by increasing the concentration of the polar solvent ethyl acetate to 80%. Anti-isomer: 1H NMR (CDCl3, 300 MHz) δ 7.26 (br s, NH, 1 H), 6.82 (br s, NH, 1 H), 5.88-5.72 (m, 1 H), 5.07 (br d, J=17 Hz, 1 H), 5.00 (br d, J=12 Hz, 1 H), 2.56-2.41 (m, 1 H), 2.36-2.17 (m, 3 H), 2.01 (s, 3 H), 1.97-1.81 (m, 2 H), 1.72-1.60 (m, 2 H), 1.32 (s, 9 H); MS (+CI): m/z for C15H26N2O2: expected 266.2; found 266.2 (M+H)+

Workup

  1. custompurified by flash column chromatography (silica gel, 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-120e757197d6423d8536ae0e95c07e2d
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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