tert-Butyl methyl(4-(5-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate → tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohex-3-enyl(methyl)carbamate

HRID 552940노트

반응식

HRID 552940 반응식
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=3)[NH:18][CH:17]=2)=[CH:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>N.CO.[Pd]>[NH2:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[C:13]1[CH2:14][CH2:15][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:11][CH:12]=1

참가 물질

5

반응물 1

HCID 57384540tert-Butyl methyl(4-(5-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate

생성물 1

HCID 57384541tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohex-3-enyl(methyl)carbamate수율 98.8%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 222Ammonia용매HCID 887Methanol용매

실험 절차

A solution of compound 81 (0.5 g, 1.364 mmol) in 2 M NH3 in methanol (20 mL) was treated with Pd—C (0.05 g) and flushed with hydrogen gas. The reaction was stirred at room temperature for over night (16 h) under hydrogen atm. (balloon pressure). The solution was filtered using celite bed and washed with CH2Cl2:methanol (1:1, 3×20 mL). The solvent was evaporated and crude was purified by column chromatography (EtOAc: Hexanes, 1:1) to obtain compound 82 (0.46 g, quantitative) as a solid in 1:2 ratio of diastereomers. 1H NMR (DMSO-d6) δ 1.38, 1.41 (2s, 9H), 1.46-1.84 (m, 6H), 2.02-2.17 (m, 2H), 2.53-2.57 (m, 1H), 2.60-2.72 (2s, 3H), 3.82-3.85 (m, 1H), 4.41 (brs, 2H), 6.42-6.50 (m, 1H), 6.66-6.68 (m, 1H), 6.85-6.87, 6.99-7.06 (2m, 2H), 10.23, 10.28 (2s, 1H); ESI-MS m/z (%): 366 (M.Na+, 8), 344 (MH+, 10), 288 (100).

후처리

  1. customflushed with hydrogen gas
  2. filtrationThe solution was filtered
  3. washwashed with CH2Cl2:methanol (1:1, 3×20 mL)
  4. customThe solvent was evaporated
  5. customcrude was purified by column chromatography (EtOAc: Hexanes, 1:1)

출처 및 근거

ORD 기록
ord-7efdf2a097004e8c921b62a745a871ab
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951940B2

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