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 552940ノート

反応式

HRID 552940 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 222Ammonia溶媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7efdf2a097004e8c921b62a745a871ab
出典データセット
uspto-grants-2011_05
特許番号
US07951940B2

反応ノート

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