tert-Butanol → tert-butyl N-{4H,5H,6H-cyclopenta[b]thiophen-2-yl}carbamate

HRID 2178983노트

반응식

HRID 2178983 반응식
[S:1]1[C:5](C(O)=O)=[CH:4][C:3]2[CH2:9][CH2:10][CH2:11][C:2]1=2.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])=CC=1.C([N:31]([CH2:34]C)CC)C.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[S:1]1[C:5]([NH:31][C:34](=[O:19])[O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:4][C:3]2[CH2:9][CH2:10][CH2:11][C:2]1=2

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 7709804H,5H,6H-cyclopenta(b)thiophene-2-carboxylic acid

생성물 1

HCID 66545155tert-butyl N-{4H,5H,6H-cyclopenta[b]thiophen-2-yl}carbamate수율 67%

실험 절차

To a solution of 4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acid (1.68 g, 9.99 mmol, 1.00 equiv) in tert-butanol (25 mL) was added DPPA (4.95 g, 17.99 mmol, 1.80 equiv) and triethylamine (3.03 g, 29.94 mmol, 3.00 equiv) at room temperature under nitrogen. The resulting solution was heated to reflux overnight in an oil bath and concentrated in vacuo. The residue was diluted with 100 mL of ethyl acetate and washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10) to provide 1.6 g (67%) of tert-butyl N-[4H,5H,6H-cyclopenta[b]thiophen-2-yl]carbamate as a white solid. MS (ES): m/z 240 (M+H)+.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight in an oil bath
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with 100 mL of ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-e8bbaff685d745199aa9251be803c92a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067948B2

반응 노트

불러오는 중…