Acetic Acid → HCID 59568806, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH2:16][CH:17]=O)[CH2:5][C@H:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[O:7][CH3:8].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C@H:6]([O:7][CH3:8])[CH2:5][C@@H:4]([C:3]([O:2][CH3:1])=[O:19])[CH2:16][CH2:17][N:30]2[CH2:29][CH2:28][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH2:32][CH2:31]2)=[CH:10][CH:11]=1Participants
Procedure
To a solution of 4(R)-(4-Fluoro-phenyl)-4-methoxy-2(S)-(2-oxo-ethyl)-butyric acid methyl ester (200 mg, 0.74 mmol) and piperazine-1-carboxylic acid tert-butyl ester (166 mg, 0.89 mmol) was added NaBH(OAc)3 (218 mg, 1.03 mmol) and AcOH (53.4 mg, 51 μL, 0.89 mmol) at room temperature. The mixture was stirred for 8 h at the room temperature. The reaction was quenched by pouring into 20 mL 5% aqueous NaOH and diluted with ethylacetate. The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated under reduced pressure and the product isolated by flash column chromatography eluting with 6% to 60% ethyl acetate/hexane to provide 270 mg of the title compound as an colorless oil.
Workup
- customThe reaction was quenched
- additionby pouring into 20 mL 5% aqueous NaOH
- additiondiluted with ethylacetate
- extractionThe mixture was extracted with ethyl acetate (3×15 mL)
- washthe combined organic layers washed with brine (2×10 mL)
- dry with materialdried over Na2SO4
- concentrationThe mixture was concentrated under reduced pressure
- customthe product isolated by flash column chromatography
- washeluting with 6% to 60% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-8e1c830c4db84a12a6ca80cf0cc7c760
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
Loading…