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

HRID 2423117ノート

反応式

HRID 2423117 の反応式
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

参加物

6

反応物 4

HCID 982104-HydroxypyrrolidineHCID 2723923Ammonium formateHCID 5049666Sodium triacetoxyborohydrideHCID 866182505-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-8526327283e149278e3c761af478b141
出典データセット
uspto-grants-2011_06
特許番号
US07960374B2

反応ノート

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