Triethylamine → HCID 178525098, 화합물

HRID 215952

반응식

HRID 215952 반응식
O=[CH:2][CH2:3][C:4]1([C:20]([O:22]C)=O)[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.Cl.[NH2:25][C@@H:26]1[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[OH:32][C@@H:29]1[CH2:30][CH2:31][C@H:26]([N:25]2[CH2:2][CH2:3][C:4]3([CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[O:11])[CH2:8][CH2:9]3)[C:20]2=[O:22])[CH2:27][CH2:28]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 588931821-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylateHCID 178479277HCID 178479277, 화합물

생성물 1

HCID 178525098HCID 178525098, 화합물수율 72.4%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate (4.80 g, 0.0150 mol), cis-4-aminocyclohexanol hydrochloride (2.5 g, 0.016 mol) and triethylamine (3.3 mL, 0.024 mol) in 1,2-dichloroethane (30.0 mL) was stirred at room temperature for 30 min. To the mixture was added sodium triacetoxyborohydride (7.9 g, 0.038 mol) with stirring. The mixture was stirred at room temperature for 1 h, then was heated at 80° C. for 2 h. After cooling, the mixture was diluted with dichloromethane, and washed with IN HCl solution, NaHCO3 (7.5%), water, and brine successively, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give benzyl 2-(cis-4-hydroxycyclohexyl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (4.20 g, 72.0%).

후처리

  1. stirringwith stirring
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. temperaturewas heated at 80° C. for 2 h
  4. temperatureAfter cooling
  5. washwashed with IN HCl solution, NaHCO3 (7.5%), water, and brine successively
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-af0a5c1b5a764d38b93dc828e33884af
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193207B2

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