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

Reaction equation

HRID 1013816 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-b516a6128eae4847a16bfe4ccc848c63
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Linked notes

Loading…