Triethylamine → (1R*,2R*,5S*,6R*)-8-Benzyl-2-[3,5-bis(trifluoromethyl)benzoyloxy]-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088116노트

반응식

HRID 2088116 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[CH2:18]([N:25]1[C@@H:30]2[C@H:31]([C:33]#[N:34])[CH2:32][C@@:26]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:27]([OH:35])[CH2:28][CH2:29]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl>[CH2:18]([N:25]1[C@@H:30]2[C@H:31]([C:33]#[N:34])[CH2:32][C@@:26]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:27]([O:35][C:6](=[O:7])[C:5]1[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=1)[CH2:28][CH2:29]2)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 69890225(1R*,2R*,5S*,6R*)-8-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

생성물 1

HCID 86586649(1R*,2R*,5S*,6R*)-8-Benzyl-2-[3,5-bis(trifluoromethyl)benzoyloxy]-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octane수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3,5-Bis(trifluoromethyl)benzoyl chloride (2.76 g, 10 mmol) was added dropwise to an ice-cold solution of (1R*,2R*,5S*,6R*)-8-benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 31; 3 g, 9.4 mmol), triethylamine (2 g, 20 mmol) and 4-N,N-dimethylaminopyridine (200 mg, 1.6 mmol) in dichloromethane (30 ml). The mixture was stirred at room temperature for 20 hours. The mixture was concentrated in vacuo then partitioned between ethyl acetate and brine. The organics were separated, dried (MgSO4), filtered and concentrated. The residue was chromatographed on silica gel eluting with 10 and 20% ethyl acetate/iso-hexanes to afford the title compound (4.87 g, 93%).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthen partitioned between ethyl acetate and brine
  3. customThe organics were separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 10 and 20% ethyl acetate/iso-hexanes

출처 및 근거

ORD 기록
ord-9ac820934b344996aafac7777a85e014
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06727249B2

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