Acetic Acid → HCID 117953322, compound

HRID 1498980Notes

Reaction equation

HRID 1498980 reaction equation
[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=O.[CH3:10][NH2:11].[CH2:12]([OH:14])[CH3:13].[C:15]([OH:18])(=O)C.[C:19]([N+:23]#[C-])([CH3:22])([CH3:21])[CH3:20]>C(O)C(F)(F)F.C(Cl)Cl>[CH2:3]([C@H:4]1[CH2:8][CH2:7][CH2:6][C@@:5]1([N:11]([CH3:10])[C:12](=[O:14])[CH3:13])[C:15]([NH:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:18])[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 23577Tert-Butyl isocyanideHCID 109205112-AllylcyclopentanoneHCID 22028356Methylamine ethanol

Product 1

HCID 117953322HCID 117953322, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a round bottom flask containing 2-(propene-3-yl)cyclopentanone (0.745 g, 6.0 mmol) was added a premixed slurry of 8 N methylamine/ethanol (3.0 mL, 24 mmol) and glacial acetic acid (1.37 mL, 24 mmol) in trifluoroethanol (3 mL). The reaction mixture is stirred for 30 minutes and then treated with t-butylisonitrile (2.04 mL, 18 mmol). After stirring for 2 days, the reaction mixture is diluted with methylene chloride (10 mL), and chromatographed using a silica gel column (175 mL). A gradient elution using 20%, 50%, and 80% mixture of ethyl acetate and heptane afforded the subject compound (559 mg, 33%) as a white crystalline solid. NMR (CDCl3): δ 5.82 (br s, 1H), 5.70 (m, 1H), 4.90-5.00 (m, 2H), 2.96 (s, 3H), 2.63 (m, 1H), 2.37 (m, 1H), 2.26 (m, 1H), 2.04 (s, 3H), 1.60-1.85 (m, 4H), 1.40-1.60 (m, 2H), 1.24 (s, 9H). MS (M+1): 281.4; MS (M+Na): 303.4.

Workup

  1. stirringAfter stirring for 2 days
  2. customchromatographed
  3. washA gradient elution

Sources & evidence

ORD record
ord-b3b6f59b98ac4a97b5f52674c308c44c
Source dataset
uspto-grants-2015_12
Patent number
US09200011B2

Reaction notes

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