Triethylamine → Benzyl N-(3-hydroxypropyl)carbamate

HRID 64931

Reaction equation

HRID 64931 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][C:21]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Procedure

In 300 ml of methylene chloride was dissolved 50 g of 3-aminopropanol, and thereto were successively added dropwise 33 g of triethylamine and 57 g of benzyloxycarbonyl chloride at -10° C. to -5° C. At the same temperature, the resulting mixture was stirred for 1 hour and then further stirred at room temperature for 1 hour. Subsequently, the reaction mixture was washed successively with 100 ml of diluted hydrochloric acid and 100 ml of water, and thereafter dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain 60 g (yield 86%) of 3-(benzyloxycarbonylamino)propanol having a melting point of 55°-56° C.

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. washSubsequently, the reaction mixture was washed successively with 100 ml of diluted hydrochloric acid and 100 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4704827fddd649e09efd5efb3119ee9d
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Linked notes

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