4-Amino-1-butanol → 4-Tert-butoxycarbonylmethylamino-1-butanol

HRID 18017

Reaction equation

HRID 18017 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>C(OCC)C>[C:12]([O:11][C:9](=[O:10])[CH2:8][NH:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 258684-Amino-1-butanolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 108458284-Tert-butoxycarbonylmethylamino-1-butanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cold (0° C.) solution of 4-hydroxybutylamine (9.1 g, 101.8 mmol) in diethyl ether (100 mL), a solution of tert-butyl bromoacetate (7.4 g, 49.3 mmol) in diethyl ether (25 mL) was added dropwise over a period of 2 hours. The reaction mixture was allowed to warm up slowly to room temperature and stirred at the temperature overnight. The product mixture was washed successively with aqueous NaHCO3, water, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate was used in the following reaction without further purification.

Workup

  1. washThe product mixture was washed successively with aqueous NaHCO3, water, and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThis intermediate was used in the following reaction without further purification

Sources & evidence

ORD record
ord-301a1819b29342888da55e194bb046f4
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Linked notes

Loading…