3-Amino-1-propanol → tert-butyl N-(3-hydroxypropyl)carbamate

HRID 1883304Notes

Reaction equation

HRID 1883304 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]([O:10][C:11](OC([O-])=O)=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(Cl)Cl>[C:6]([O:10][C:11]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 22064466Tert-butyldicarbonate

Product 1

HCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-aminopropanol (15 mL, 0.20 mol) in methylene chloride (50 mL) at rt was treated with t-butylpyrocarbonate (42.02 g, 1 equiv) in methylene chloride (25 mL), dropwise over 2 h. After stirring overnight the mixture was evaporated, flushed with heptane (3×), and dried in vacuo to give the product as a thick oil (34.31 g, 100%). 1H NMR δ 1.48 (s, 9H), 3.12 (br, 1H), 3.22 (q, J=7.5 Hz, 2H), 3.60 (q, J=7.8 Hz, 2H), 4.81 (br, 1H). MS (DCl) 176 (MH)+. Anal calcd for C8H17NO3: C-54.84, H-9.78, N-7.99. Found: C-54.80, H-9.82, N-7.97.

Workup

  1. customwas evaporated
  2. customflushed with heptane (3×)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5cbacb9660144f059b376d1d400150f7
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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