Reacción #1153156

Ecuación de reacción

(2S,3S)-(−)-3-amino-2-phenylpiperidine

benzyl chloroformate

diisopropylethylamine

→

title compound

Rendimiento 80.2%

(2S,3S)-3-Benzyloxycarbonylamino-2-phenylpiperidine

Rendimiento 80.2%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by addition of water
2. 2
   OtroThe mixture was separated
3. 3
   LavadoThe organic layers were successively washed with a portion of brine
4. 4
   Secadodried over sodium sulfate
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by flash chromatography (5% methanol in methylene chloride)

Procedimiento

To a solution of (2S,3S)-(−)-3-amino-2-phenylpiperidine (152 mg, 0.86 mmole) (L-tartaric acid salt, [a]D=−57.1 (EtOH, c=0.1138)) in methylene chloride (10 mL) at room temperature was added benzyl chloroformate (0.123 mL, 0.86 mmole) and diisopropylethylamine (0.45 mL, 2.58 mmole). The reaction was stirred for 16 hours and was then diluted with methylene chloride and quenched by addition of water. The mixture was separated and the aqueous was reextracted with 2 additional aliquots of methylene chloride. The organic layers were successively washed with a portion of brine, dried over sodium sulfate, combined and evaporated. The residue was purified by flash chromatography (5% methanol in methylene chloride) to afford 214 mg (80%) of the title compound. NMR (CDCl3): δ 1.55 (br, d, J=9 Hz, 1 H), 1.6-1.9 (m, 2 H), 2.02 (br. d, J=9 Hz, 1 H), 2.79 (dd, J=9 and 10 Hz, 1 H), 3.22 (dd, J=1 and 10 Hz, 1 H), 3.91 (br. s, 1 H), 4.01 (dd, J=1 and 8 Hz, 1 H), 4.89 (s, 2 H), 5.65 and 5.88 (2 br. s, 1 H), 7.1-7.4 (m, 10 H).

Fuente