2,2,2-Trifluoroethanol → HCID 89514299, compound

HRID 1778566Notes

Reaction equation

HRID 1778566 reaction equation
[CH3:1][O:2][C:3]1([O:13][CH3:14])[CH2:6][CH:5]([C:7](=O)[CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:4]1.[C:15]([O-:18])(=O)[CH3:16].[NH4+:19].[C:20]([N+:24]#[C-])([CH3:23])([CH3:22])[CH3:21].FC(F)(F)[CH2:28][OH:29]>C(OCC)(=O)C>[C:15]([NH:19][C:7]([CH:5]1[CH2:6][C:3]([O:13][CH3:14])([O:2][CH3:1])[CH2:4]1)([CH2:8][CH2:9][CH:10]=[CH2:11])[C:28]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:29])(=[O:18])[CH3:16]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 89527308HCID 89527308, compound

Product 1

HCID 89514299HCID 89514299, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(3,3-dimethoxycyclobutyl)pent-4-en-1-one (3.0, 15.1) was dissolved in 2,2,2-trifluoroethanol (7 mL). Ammonium acetate (4.66 g, 60.5 mmol) and tert-butyl isocyanide (3.40 mL, 30.3 mmol) were added and the reaction was stirred 3 days at room temperature. The reaction was diluted with ethyl acetate, washed successively with water, saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane to afford the desired product (4.04 g, 79%). Rf 0.16 (50% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 7.10 (br s, 1H), 6.71 (br s, 1H), 5.83-5.69 (m, 1H), 5.03-4.91 (m, 2H), 3.14 (s, 6H), 2.91-2.72 (m, 2H), 2.39-2.24 (m, 2H), 2.13-1.79 (m, 7H), 1.53-1.33 (m, 10H). ESI MS found for C18H32N2O4 m/z [363.0 (M+Na+)].

Workup

  1. washwashed successively with water, saturated aqueous sodium chloride
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-29e66c6028c3464f951c29ee8a769c6d
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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