Benzylamine → tert-butyl (3aR,7aS)-2-(benzylamino)-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate

HRID 2053539ノート

反応式

HRID 2053539 の反応式
CS[C:3]1[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:11]([O:10][C:8]([N:7]1[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=[C:3]1[NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

参加物

4

反応物 2

HCID 7504BenzylamineHCID 86596330cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic Acid, Tert-Butyl Ester

生成物 1

HCID 68569663tert-butyl (3aR,7aS)-2-(benzylamino)-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate収率 84.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), benzylamine (0.5 mL, 4.6 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 207 mg of the product 189. 1H NMR (CDCl3) δ 8.56 (s, 1H), 7.50-7.20 (m, 5H), 5.15-4.95 (m, 2H), 4.35-4.05 (m, 2H), 2.85-2.55 (m, 1H), 2.25-2.05 (m, 1H), 1.90-1.05 (m, 15H); MS: m/z 330 (M++1).

後処理

  1. custom(reaction block) overnight
  2. temperatureThe reaction mixture is cooled to RT
  3. washwashed with 0.1N HCl, and brine
  4. customThe solvent is evaporated
  5. customthe residue triturated with EtOAc
  6. filtrationthe insoluble material filtered

出典と根拠

ORDレコード
ord-84efdb5d5dae460a81073ea222b46092
出典データセット
uspto-grants-2008_02
特許番号
US07326792B2

反応ノート

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