반응 #2358492

ord-2ac0e660763741e087333902bff58fd7

반응 방정식

CN(C)C=C1C(=O)N(C(=O)OC(C)(C)C)C2C=CCC12
tert-butyl-3-(dimethylaminomethylene)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate
Cl
hydrochloric acid
C1COCCO1
dioxane
CC(C)(C)OC(=O)N1C(=O)C(=CO)C2CC=CC21
desired compound
수율 93.0%
CC(C)(C)OC(=O)N1C(=O)C(=CO)C2CC=CC21
Tert-butyl-3-(hydroxymethylene)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate
수율 93.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척washed with water and brine
  2. 2
    기타dried
  3. 3
    농축concentrated

실험 절차

A solution of tert-butyl-3-(dimethylaminomethylene)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate III-1 (120 mg, 0.43 mmol) in dioxane (9 mL) was stirred with hydrochloric acid (2 M, 0.86 mL, 1.72 mmol) for 15 h at room temperature. The solution was diluted with ethyl acetate, washed with water and brine, dried, concentrated giving the desired compound as a colorless oil (101 mg, 93%); 1H NMR (400 MHz, CDCl3) 9.92 (1H, d), 7.05 (1H, d), 6.91 (1H, m), 5.71 (1H, m), 5.07 (1H, d), 3.46 (1H, dt), 2.87 (1H, dd), 2.31 (1H, m), 1.55 (9H, s). LCMS (Method A): 0.79 min; ES−250 (M−H+).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09119398B2uspto-grants-2015_09