Reaction equation
[C:1]([N:9]1[CH2:17][CH2:16][CH:12]([C:13](O)=[O:14])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CN(C=O)C.O>[OH:14][CH2:13][CH:12]1[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2 g of 1-benzoylisonipecotic acid (Step A) in 50 mL THF at 0° C. were added 1.47 g of triethylamine and 1.99 g of isobutyl chloroformate. The reaction was stirred for 1 h at 0° C. To a solution of 1.10 g of sodium borohydride in 30 mL DMF at 0° C. was slowly added the above THF mixture. The reaction was again stirred for 1 h at 0° C. Water (80 mL) was slowly added to the reaction and the mixture was extracted 5×80 mL ethyl acetate and the combined organic layers were dried over magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 1:1 hexane : ethyl acetate followed by hexane : ethyl acetate: methanol, 50:50:5 to give 1.865 g of the title compound.
Workup
- stirringThe reaction was again stirred for 1 h at 0° C
- extractionthe mixture was extracted 5×80 mL ethyl acetate
- dry with materialthe combined organic layers were dried over magnesium sulfate
- customThe solvent was then evaporated under reduced pressure
- customThe residue was purified by flash chromatography with 1:1 hexane
Sources & evidence
- ORD record
- ord-ac9768a399e142d29cfd64358aaa3407
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06358979B1
Linked notes
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