تفاعل #506609

معادلة التفاعل

1-boc-4-piperidone

benzyl 1-piperazine-carboxylate

HOAc

Sodium triacetoxyborohydride

→

title compound

Phenylmethyl 4-(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)-1-piperazinecarboxylate

المذيبات

DCE

ظروف التفاعل

المعالجة

1. 1
   أخرىis consumed
2. 2
   أخرىThe reaction was quenched with NaHCO3
3. 3
   استخلاصextracted with DCM (3×)
4. 4
   تجفيفCombined organics were dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   workup.ADDITIONDiluted crude material with DCM
8. 8
   أخرىpurified by column chromatography

الإجراء التجريبي

Combined 1-boc-4-piperidone (10.0 g, 50.2 mmol), benzyl 1-piperazine-carboxylate (19.3 mL, 100.4 mmol), HOAc (4.3 mL, 75.3 mmol) and TEA (7.0 mL, 50.2 mmol) in DCE (150 mL) were stirred at rt. Sodium triacetoxyborohydride was added (16.0 g, 75.3 mmol). The reaction was stirred for 3 h at which point TLC shows starting material is consumed. The reaction was quenched with NaHCO3 and extracted with DCM (3×). Combined organics were dried over MgSO4, filtered and concentrated in vacuo. Diluted crude material with DCM and adsorbed onto a prepacked silica gel solid loading cartridge and purified by column chromatography to give title compound of step A (yield not obtained). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.04-7.52 (m, 5H), 5.02 (s, 2H), 3.74-4.05 (m, 2H), 3.06-3.49 (m, 4H), 2.63 (br. s., 2H), 2.22-2.50 (m, 5H), 1.64 (d, J=12.1 Hz, 2H), 1.07-1.27 (m, 2H), 1.34 (s, 9H).

المصدر