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

HRID 18746노트

반응식

HRID 18746 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

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, 1 H), 7.50-7.20 (m, 5 H), 5.15-4.95 (m, 2 H), 4.35-4.05 (m, 2 H), 2.85-2.55 (m, 1 H), 2.25-2.05 (m, 1 H), 1.90-1.05 (m, 15 H); MS: m/z 330 (M++1).

후처리

  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

출처 및 근거

ORD 기록
ord-065a3fafad52419c824992490eca7601
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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