1-Amino-2-propanol → HCID 12384307, compound

HRID 1787857Notes

Reaction equation

HRID 1787857 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:10]([O:9][C:7]([NH:1][CH2:2][CH:3]([OH:5])[CH3:4])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 41-Amino-2-propanolHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 12384307HCID 12384307, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1-amino-2-propanol (1) (4.6 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, the product was extracted with CH2Cl2 (3×20 mL), dried over Na2SO4 and concentrated. The residue was purified by a flash chromatography on SiO2 eluting with 10:1 hex:EtOAc, followed by EtOAc to afford 1-benzyloxycarbonylamino-2-propanol (12.9 g, 100%) as an oil. 1H NMR (CDCl3): □ 7.30 (m, 5H), 5.90 (s, 1H), 5.06 (s, 2H), 3.95 (s, 1H), 3.31 (m, 1H), 3.04 (m, 1H), 1.2 (d, 3H)

Workup

  1. extractionthe product was extracted with CH2Cl2 (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by a flash chromatography on SiO2 eluting with 10:1 hex

Sources & evidence

ORD record
ord-0846c3af3db74fb580a9cab8a8c1a031
Source dataset
uspto-grants-2009_03
Patent number
US07511063B2

Reaction notes

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