Benzyl chloroformate → HCID 54272252, compound

HRID 895277Notes

Reaction equation

HRID 895277 reaction equation
[NH2:1][CH2:2][C@@H: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]>C1C=CC=CC=1>[CH2:10]([O:9][C:7]([NH:1][CH2:2][C@@H:3]([OH:5])[CH3:4])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 7311736(S)-(+)-1-Aminopropan-2-ol

Product 1

HCID 54272252HCID 54272252, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of (S)-1-amino-2-propanol (9.76 g, 130 mmol) in anhydrous benzene (60 mL) at 0° C. was added benzyl chloroformate (10.23 g, 60 mmol) in anhydrous benzene (120 mL) slowly, in portions, over a period of 20 min while vigorously stirring under an atmosphere of nitrogen. The mixture was stirred for 1 hour at 0° C., then allowed to warm to room temperature and stirred for a further 2 hours. The mixture was washed with water (2×) and brine (2×) before the organic layer was dried over anhydrous MgSO4. Evaporation of all solvent gave the title product as an oil. 1H NMR (CDCl3) δ 1.22 (d, 3H,) 2.40 (bs, 1H), 3.07 (m, 1H), 3.37 (m, 1H)), 3.94 (m, 1H), 5.16 (s, 2H), 5.27 (m, 1H), 7.38 (m, 5H). MS m/z (electrospray) 232 [M+23]+ (100%), 166 (96).

Workup

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. stirringstirred for a further 2 hours
  3. washThe mixture was washed with water (2×) and brine (2×) before the organic layer
  4. dry with materialwas dried over anhydrous MgSO4
  5. customEvaporation of all solvent

Sources & evidence

ORD record
ord-0c37411e0bfc45549dbe8a82400d27a8
Source dataset
uspto-grants-2005_07
Patent number
US06914158B2

Reaction notes

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