Acetic Acid → HCID 57741529, compound

HRID 416017Notes

Reaction equation

HRID 416017 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:28]5[CH2:33][CH:32]6[CH2:34][CH:29]5[CH2:30][NH:31]6)=[O:27])=[CH:22][CH:21]=4)=[CH:15][C:14]=3[Cl:35])[C:8]2=[O:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:37][C:38]([CH3:40])=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([N:28]5[CH2:33][C@@H:32]6[CH2:34][C@H:29]5[CH2:30][N:31]6[CH:38]([CH3:40])[CH3:37])=[O:27])=[CH:22][CH:21]=4)=[CH:15][C:14]=3[Cl:35])[C:8]2=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 66621762HCID 66621762, compound

Product 1

HCID 57741529HCID 57741529, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of chiral 1-cyclohexyl-3-[3,5-dichloro-4′-(2,5-diaza-bicyclo[2.2.1]heptane-2-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-one (0.096 g, 0.18 mmol) in methanol (3 mL) and acetone (0.105 g, 1.81 mmol) with sodium cyanoborohydride (0.055 g, 0.88 mmol) and then acetic acid (0.057 g, 0.94 mmol). Stir the mixture for 3 hours at room temperature under a nitrogen atmosphere, dilute with ethyl acetate and wash with saturated sodium bicarbonate then water. Dry the organic layer with sodium sulfate and purify the crude product by silica gel chromatography using a gradient of 0 to 10% methanol in dichloromethane to afford 71 mg (68%) of the title compound: MS (m/z): 568 (M+).

Workup

  1. washwash with saturated sodium bicarbonate
  2. dry with materialDry the organic layer with sodium sulfate
  3. custompurify the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-8dbb80cfd92e48f7ae82e694b25e8dcd
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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