4-Hydroxypyrrolidine → 4-[(3-hydroxypyrrolidin-1-yl)methyl]-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 2423117노트

반응식

HRID 2423117 반응식
C([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:13]=[CH:12][C:11]=2[C:10]=1[CH:27]=O)C1C=CC=CC=1.[OH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])=O.[NH4+]>ClCCCl>[OH:29][CH:30]1[CH2:34][CH2:33][N:32]([CH2:27][C:10]2[C:9]([OH:8])=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][N:14]3[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:20])[CH2:31]1

참가 물질

6

반응물 4

HCID 982104-HydroxypyrrolidineHCID 2723923Ammonium formateHCID 5049666Sodium triacetoxyborohydrideHCID 866182505-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde2회

생성물 1

HCID 595135774-[(3-hydroxypyrrolidin-1-yl)methyl]-1-(phenylsulfonyl)-1H-indol-5-ol수율 91.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 5-(benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (Intermediate 4, 100 mg, 0.250 mmol) in DCE (3 mL) was added 3-hydroxypyrrolidine, (33 mg, 0.38 mmol) and sodium triacetoxyborohydride (0.16 g, 0.77 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in MeOH (2 mL) and Pd/C 10 wt. % (0.020 g, 0.019 mmol) was added and the mixture was flushed with N2 gas. Ammonium formate (0.050 g, 0.80 mmol) was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was taken up in CHCl3/H2O, and the mixture was washed with water and brine, dried (MgSO4) and the solvent was removed under reduced pressure to give 4-[(3-hydroxypyrrolidin-1-yl)methyl]-1-(phenylsulfonyl)-1H-indol-5-ol (85 mg) as an oil. MS m/z 373 [M+H]+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in MeOH (2 mL)
  3. additionPd/C 10 wt. % (0.020 g, 0.019 mmol) was added
  4. customthe mixture was flushed with N2 gas
  5. stirringthe reaction mixture was stirred at room temperature overnight
  6. customThe solvent was removed under reduced pressure
  7. washthe mixture was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-8526327283e149278e3c761af478b141
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960374B2

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