反应详情

To a stirred solution of (S)-1-(3-chlorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (31 mg, 0.10 mmol) and (S)-tert-butyl 1-(p-nitrophenoxycarbonylamino)-3-cyclohexylpropan-2-ylcarbamate (40 mg, 0.10 mmol) in MeCN (1 mL) and CH2Cl2 (1 mL) was added DIEA (50 μL, 0.28 mmol). The mixture was stirred at rt for 20 h, diluted with ether (90 mL), washed with 5% aq HCl (20 mL) and 1 M aq NaOH (20 mL) and dried over MgSO4. Removal of the solvent left an oil (82 mg) which was applied to a 2-g silica SPE cartridge which was eluted sequentially with 10, 25, 50, 75 and 100% ethyl acetate in hexanes (15 mL of each) to afford 5 fractions. The 4th fraction was concentrated to afford tert-butyl (S)-1-((R)-3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclohexylpropan-2-ylcarbamate (29 mg, 49%) as an oil.

1. washwashed with 5% aq HCl (20 mL) and 1 M aq NaOH (20 mL)
2. dry with materialdried over MgSO4
3. customRemoval of the solvent
4. waitleft an oil (82 mg) which
5. washwas eluted sequentially with 10, 25, 50, 75 and 100% ethyl acetate in hexanes (15 mL of each)
6. customto afford 5 fractions
7. concentrationThe 4th fraction was concentrated