반응 #1077581

반응 방정식

4,4-bis-(4-fluorophenyl)-butylamine

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

NaBH(OAc)3

→

desired product

수율 70.3%

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

수율 70.3%

용매

EtOAc

반응 조건

후처리

1. 1
   workup.STIRRINGstirred overnight at room temperature
2. 2
   세척washed with saturated bicarbonate solution and brine
3. 3
   건조dried over Na2SO4
4. 4
   농축concentrated
5. 5
   기타The crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2

실험 절차

4,4-bis-(4-fluorophenyl)-butylamine (200 mg, 0.77 mmol) was dissolved in CH,2Cl2 (5 mL), treated with (S)-(1-formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester (229 mg, 1.0 mmol), stirred for 30 minutes, then cooled to 0° C., treated with NaBH(OAc)3 (245 mg, 1.16 mmol), and stirred overnight at room temperature. The reaction was diluted with EtOAc (100 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2 to give 257 mg (70%) of the desired product as an oil. MS: 475.4 (M+1 for C28H40N2O2F2); an oil; TLC (SiO2), Rf 0.26 (4% MeOH/CH2Cl2); HPLC (1:1 CH3CN/H2O with 0.1% TFA, C-18 column) 100%, RT=15.013 min.

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