Triethylamine → Benzyl N-(3-hydroxypropyl)carbamate

HRID 1626302Notes

Reaction equation

HRID 1626302 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C(Cl)Cl.C(OCC)C.O>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 10387Benzyl chloroformate

Product 1

HCID 562256Benzyl N-(3-hydroxypropyl)carbamateYield 107.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3-Aminopropan-1-ol (10 g, 133 mmol) was dissolved in methylene chloride (100 ml) at 0° C. Triethylamine (9 ml, 65 mmol) and CbzCl (10 ml, 66.8 mmol) were added slowly to the resulting solution at 0° C. and warmed to room temperature. The reaction mixture thus obtained was stirred for 1 hour at room temperature, and then diethyl ether (100 ml) and water (50 ml) were poured into the resulting solution. With diethyl ether normal work-up was taken, dried with magnesium sulfate. After evaporation the volatile material, the residue was purified with normal phase preparative column to produce the title compound (15 g, 95%) as colorless oil.

Workup

  1. customThe reaction mixture thus obtained
  2. dry with materialdried with magnesium sulfate
  3. customAfter evaporation the volatile material
  4. customthe residue was purified with normal phase preparative column

Sources & evidence

ORD record
ord-eece88bc103244529d81cac89c07a738
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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