Sodium Carbonate → benzyl N-(2-hydroxybutyl)carbamate

HRID 1385184Notes

Reaction equation

HRID 1385184 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:11]([O:10][C:8]([NH:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 261071-Amino-2-butanol

Product 1

HCID 18667998benzyl N-(2-hydroxybutyl)carbamateYield 100.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1-amino-2-butanol (5.5 g, 61.8 mmol), benzyl chloroformate (11.5 g, 67.6 mmol) and sodium carbonate (7.16 g, 67.7 mmol) in water (50 mL) was stirred at 0° C. for 3 h. Water (50 mL) was added to the reaction mixture and the product was extracted with methylene chloride (3×20 mL). The methylene chloride extract was dried over Na2SO4 and concentrated. The residue was passed through a short column (SiO2, hexanes : ethyl acetate /10:1; then ethyl acetate) to afford 1-benzyloxycarbonylamino-2-butanol (13.9 g, 100%) as a liquid.

Workup

  1. extractionthe product was extracted with methylene chloride (3×20 mL)
  2. extractionThe methylene chloride extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e5560b3c4af4df1a3c2916af1cd77ea
Source dataset
uspto-grants-2001_07
Patent number
US06262096B1

Reaction notes

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