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

HRID 276271

反応式

HRID 276271 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a073b20e851841b996bb72b3100effb1
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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