3-Amino-1-propanol → Benzyl N-(3-hydroxypropyl)carbamate

HRID 2227716Notes

Reaction equation

HRID 2227716 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]>C(Cl)Cl>[C:7]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 10387Benzyl chloroformate

Product 1

HCID 562256Benzyl N-(3-hydroxypropyl)carbamateYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A CH2Cl2 solution (300 mL) of 3-aminopropanol (10 g, 0.133 mole) and TEA (20 g, 0.2 mole) was cooled to 0° C., followed by slow addition of CH2Cl2 solution (25 mL) of benzyl chloroformate (25 g, 0.147 mole). The resulting solution was gradually warmed to room temperature. The stirring was continued at room temperature overnight. The reaction mixture was washed with H2O, dried and purified by flash column chromatography (on silica gel, CH3OH—CH2Cl2) to yield 16.4 g, 58.9% of title compound. 1H NMR (CDCl3): δ 7.26-740 (m, 5H), 5.10 & 5.0-5.10 (s+m, 3H), 3.68 (q, 2H), 3.36 (q, 2H), 2.58 (t, 1H), 1.70 (p, 2H).

Workup

  1. washThe reaction mixture was washed with H2O
  2. customdried
  3. custompurified by flash column chromatography (on silica gel, CH3OH—CH2Cl2)

Sources & evidence

ORD record
ord-e80d5c8e30b74d9f9a710733e850459e
Source dataset
uspto-grants-2002_07
Patent number
US06414127B1

Reaction notes

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