Trifluoroacetic acid → 10-Phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane

HRID 712946노트

반응식

HRID 712946 반응식
[C:1]1([CH:7]2[O:24][C:11]3([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH2:10][N:9]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([CH:7]2[O:24][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][N:9]([CH2:25][C:26]([F:28])([F:29])[F:27])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 70872528HCID 70872528, 화합물

생성물 1

HCID 6831077510-Phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To tert-butyl 10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (779 mg, 1.86 mmol) in dichloromethane (5 mL) was added 2,2,2-trifluoroacetic acid (5 mL, 64.90 mmol) at room temperature. The reaction mixture was stirred for 40 minutes, then diluted with dichloromethane (75 mL) and the organic solution was washed with saturated sodium bicarbonate (twice) and then brine. The organic layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo to give 10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane as an amber oil (585 mg, 99%). ESI-MS m/z calc. 314.2. found 315.3 (M+1)+; Retention time: 1.29 minutes (3 min run). 1H NMR (400 MHz, CD3CN) δ 7.44-7.25 (m, 5H), 4.82 (dd, J=10.6, 2.8 Hz, 1H), 3.74 (br s, 1H), 3.06 (q, J=9.8 Hz, 2H), 3.02-2.91 (m, 2H), 2.88 (dd, J=11.2, 1.5 Hz, 1H), 2.85-2.74 (m, 3H), 2.34 (d, J=14.8 Hz, 1H), 2.28 (dt, J=10.9, 5.3 Hz, 2H), 1.76-1.64 (m, J=16.0, 8.7, 5.3 Hz, 1H), 1.64-1.52 (m, 2H).

후처리

  1. washthe organic solution was washed with saturated sodium bicarbonate (twice) and then brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-334f56f8e1904dfca35def3addec77cc
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181273B2

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