3-Amino-1-propanol → N,O-bis-(benzyloxycarbonyl)-3-aminopropanol

HRID 903608Notes

Reaction equation

HRID 903608 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH2:13][CH2:14][CH2:15][OH:16]>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 10387Benzyl chloroformate

Product 1

HCID 20236395N,O-bis-(benzyloxycarbonyl)-3-aminopropanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzyl chloroformate (47 ml.) was added dropwise to a stirred solution of 3-aminopropanol (11.4 ml) in pyridine (150 ml) at 0°. The mixture was then stirred at room temperature overnight. This was poured into ice-water (300 ml.) and extracted with ethyl acetate (3×200 ml). The organic extract was washed with hydrochloric acid (5m, 3×400 ml), dried with anhydrous sodium carbonate-magnesium sulphate and evaporated to give the desired compound as an oil contaminated with a little dimethylcarbonate (30.23 g).

Workup

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. extractionThe organic extract
  3. washwas washed with hydrochloric acid (5m, 3×400 ml)
  4. dry with materialdried with anhydrous sodium carbonate-magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-bc0aa860778f47f78ef3e94a99aa9fd1
Source dataset
uspto-grants-1980_10
Patent number
US04228174

Reaction notes

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