Diethyl Pyrocarbonate → tert-butyl (1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylcarbamate

HRID 550259

반응식

HRID 550259 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.CCOC(OC(O[CH2:34][CH3:35])=O)=O.C(=O)([O-])O.[Na+].[CH3:41][N:42]([CH:44]=O)C>>[C:9]1([C@H:41]2[C@H:22]3[CH2:24][CH2:23][N:20]([C:15]([C@H:10]4[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]4[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17])[C@H:21]3[C:35]3[CH:34]=[CH:3][CH:1]=[CH:2][C:44]=3[NH:42]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 5

HCID 3051Diethyl PyrocarbonateHCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 1512489(1S,2R)-2-(((tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

생성물 1

HCID 57846948tert-butyl (1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylcarbamate수율 50%

실험 절차

To a solution of the compound (13 g, 40.2 mmol) synthesized in Reference Example 8 and (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (11.7 g, 48.2 mmol) in DMF (200 ml) were added dropwise triethylamine (16.9 ml, 121 mmol) at 0° C. and subsequently a solution of DEPC (6.74 ml, 40.2 mmol) in DMF (40 ml). The mixture was stirred at the same temperature for 30 min., saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine and dried (over anhydrous MgSO4). After concentration under reduced pressure, the obtained residue was subjected to column chromatography using silica gel, and eluted with hexane-ethyl acetate (10:1-1:1, v/v). tert-Butyl (1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexylcarbamate (9.57 g, 50%) was obtained as a colorless amorphous form from the first object eluted fraction.

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (over anhydrous MgSO4)
  4. concentrationAfter concentration under reduced pressure
  5. washeluted with hexane-ethyl acetate (10:1-1:1

출처 및 근거

ORD 기록
ord-d7e1fb2726e04cf78bb5a9c55199bf5a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943770B2

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