تفاعل #1077545

معادلة التفاعل

HCl

sodium cyanoborohydride

(S)-(1-Formyl-3-methyl-butyl)-carbamic acid tert-butyl ester

1-bis(4-fluorophenyl)methyl piperazine

→

pure titled compound

المردود 41.3%

(S)-(1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-ylmethyl}-3-methyl-butyl)-carbamic acid tert-butyl ester

المردود 41.3%

المذيبات

methanol

HOAc

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at ambient temperature for 24 hours at which time TLC
3. 3
   أخرىuntil bubbling
4. 4
   استخلاصThe resulting mixture was extracted with EtOAc (3×25 mL)
5. 5
   غسيلthe combined organic solution was washed with brine (50 mL)
6. 6
   تجفيفdried over MgSO4
7. 7
   تركيزThe solution was concentrated in vacuo
8. 8
   أخرىaffording an amber oil
9. 9
   أخرىThe crude product was further purified by flash chromatography (20%-30% EtOAc in hexanes)

الإجراء التجريبي

(S)-(1-Formyl-3-methyl-butyl)-carbamic acid tert-butyl ester (0.39 mg, 1.8 mmol) and 1-bis(4-fluorophenyl)methyl piperazine (0.50 g, 1.7 mmol) were dissolved in 1% HOAc in methanol (8 mL) under nitrogen atmosphere at ambient temperature. After stirring at that temperature for 1 hour, a solution of sodium cyanoborohydride (250 mg, 3.6 mmol) in methanol was added. The resulting reaction mixture was stirred at ambient temperature for 24 hours at which time TLC showed no starting aldehyde. 3N aqueous HCl was added in 5 mL portions until bubbling subsided; pH was adjusted to 8 with saturated aqueous NaHCO3 solution. The resulting mixture was extracted with EtOAc (3×25 mL), the combined organic solution was washed with brine (50 mL) and dried over MgSO4. The solution was concentrated in vacuo affording an amber oil. The crude product was further purified by flash chromatography (20%-30% EtOAc in hexanes) affording 342 mg (41%) of the pure titled compound as a clear oil. APCI-MS m/z 488.3 (MH+).

المصدر