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

HRID 276271Notes

Reaction equation

HRID 276271 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a073b20e851841b996bb72b3100effb1
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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