Dimethylformamide → tert-butyl N-(3-hydroxypropyl)carbamate

HRID 583664Notes

Reaction equation

HRID 583664 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].CCN(CC)CC.CN(C=O)C.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>CCOCC>[C:19]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-aminopropanol 8-1 (Aldrich) (15 g, 0.2 mol), NEt3 (42 mL, 0.3 mol) and DMF (400 mL) at 0° C. was added BOC2O (52 g, 0.24 mol). After stirring at 0° C. for 6 h the reaction mixture was diluted with ether and then washed with H2O (2×), sat. NaHCO3, 5% KHSO4 and brine, dried (MgSO4) and concentrated to give 8-2 as a colorless oil.

Workup

  1. washwashed with H2O (2×), sat. NaHCO3, 5% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab0e49bfead5406aa9bf2137493ce4f9
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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