Sodium triacetoxyborohydride → (R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-pyrrolidin-2-one

HRID 1013816

反応式

HRID 1013816 の反応式
[CH2:1]([C@@H:8]1CO[C:10](=O)[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16]C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[NH:37]1C2CCCC(N)C=2C=[N:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH2:28]([O:27][C:23]1[CH:22]=[C:21]([Cl:35])[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:10][N:9]([CH:8]3[CH2:1][CH2:2][CH2:7][C:6]4[NH:38][N:37]=[CH:4][C:5]3=4)[C:14]2=[O:36])=[C:25]([Cl:26])[CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 219419414,5,6,7-tetrahydro-1H-indazol-4-amineHCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

生成物 1

HCID 67316437(R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-pyrrolidin-2-one

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde, Preparation 38, (2 g, 3.81 mmol) in DCE (75 mL) at room temperature, add 4,5,6,7-tetrahydro-1H-indazol-4-ylamine (0.66 g, 4.77 mmol) and sodium triacetoxy borohydride (2.42 g, 11.45 mmol). Stir the reaction at room temperature for 12 h and at 50° C. for 1 hour. Cool the reaction, dilute with dichloromethane and wash with water. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 50% ethyl acetate in hexane to 100% ethyl acetate to afford 1.32 g of the title compound. MS (m/z): 470 (M+).

後処理

  1. customthe reaction at room temperature for 12 h
  2. temperatureCool
  3. customthe reaction
  4. washwash with water
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 50% ethyl acetate in hexane to 100% ethyl acetate

出典と根拠

ORDレコード
ord-b516a6128eae4847a16bfe4ccc848c63
出典データセット
uspto-grants-2011_07
特許番号
US07981918B2

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