Hydrochloric Acid → N-(1-(5-amino-2-benzyloxyphenyl)-1-methylethyl)carbamic acid t-butyl ester

HRID 1861971노트

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HRID 1861971 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.C(Cl)(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:12]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22981078N-(1-(2-benzyloxy-5-nitrophenyl)-1-methylethyl)carbamic acid t-butyl ester

생성물 1

HCID 22981125N-(1-(5-amino-2-benzyloxyphenyl)-1-methylethyl)carbamic acid t-butyl ester수율 94.3%

시약·촉매·용매 3

HCID 11791229Dichloronickel;hexahydrate촉매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

To a mixture of the compound (100 mg) obtained in Example 565, nickel (II) chloride hexahydrate (123 mg) and methanol (6 ml), sodium borohydride (39 mg) was added. The reaction mixture was stirred at room temperature for 10 min; then, 2 N HCl was added and a saturated aqueous sodium bicarbonate solution and chloroform were also added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:2) to give 87 mg of the titled compound (yield, 94%).

후처리

  1. additionwas added
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:2)

출처 및 근거

ORD 기록
ord-7f84a9a7e5e84b4aa5ba1b129490f017
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534546B1

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