Hydrochloric Acid → N-(tert-butoxycarbonyl)-N-(2-hydroxyethyl)-1-amino-2-methylprop-2-ene

HRID 276271

반응식

HRID 276271 반응식
C([O:5][C:6](=O)[CH2:7][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:10]([CH3:12])=[CH2:11])(C)(C)C.[BH4-].[Li+].O.Cl>CCOCC>[C:16]([O:15][C:13]([N:8]([CH2:7][CH2:6][OH:5])[CH2:9][C:10]([CH3:12])=[CH2:11])=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 18316043N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester

생성물 1

HCID 18316517N-(tert-butoxycarbonyl)-N-(2-hydroxyethyl)-1-amino-2-methylprop-2-ene수율 57%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester (0.26 g, 0.93 mmol) in Et2O (3 mL) was treated with lithium borohydride (0.011 g), then stirred at room temp. overnight. To the resulting mixture was added water (2 mL), then a 1N HCl was added dropwise until gas evolution stopped. The organic phase was washed with a saturated NaHCO3 solution (20 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, gradient from 10% EtOAc/hex to 50% EtOAc/hex) to give N-(tert-butoxycarbonyl)-N-(2-hydroxyethyl)-1-amino-2-methylprop-2-ene (0.113 g, 57%): TLC (10% EtOAc/hex) Rf0.66.

후처리

  1. washThe organic phase was washed with a saturated NaHCO3 solution (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography (SiO2, gradient from 10% EtOAc/hex to 50% EtOAc/hex)

출처 및 근거

ORD 기록
ord-a073b20e851841b996bb72b3100effb1
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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