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

HRID 1861971Notes

Reaction equation

HRID 1861971 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-7f84a9a7e5e84b4aa5ba1b129490f017
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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