Cyclobutanone → 6-Cyclobutyl-2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

HRID 1364157노트

반응식

HRID 1364157 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:20]=[C:19]3[C:13]([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:21]1(=O)[CH2:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:21]1([N:16]2[CH2:17][CH2:18][C:19]3=[CH:20][N:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=4)[N:12]=[C:13]3[CH2:14][CH2:15]2)[CH2:24][CH2:23][CH2:22]1

참가 물질

7

반응물 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669307912-[4-(Methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

생성물 1

HCID 160488376-Cyclobutyl-2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 38) (4 mg, 0.014 mmol) in dichloromethane (2 ml) was added cyclobutanone (7 mg, 0.096 mmol) and acetic acid (1 drop). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (20 mg, 0.096 mmol) was added and stirring continued overnight. The resulting reaction mixture was diluted with methanol and purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo to afford the title compound (E28). MS (ES+) m/e 346 [M+H]+.

후처리

  1. stirringstirring continued overnight
  2. customThe resulting reaction mixture
  3. custompurified by SCX
  4. washeluting with methanol
  5. customsolvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-030525f36bb141cfa495dc65248354e2
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888347B2

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