Potassium Carbonate → Tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamate

HRID 1672100Notes

Reaction equation

HRID 1672100 reaction equation
[C:1]([N:8]([CH3:10])[OH:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]O.[C:18]([O-])([O-])=[O:19].[K+].[K+]>CN(C=O)C.[Li+].[Br-]>[OH:19][CH2:18][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:9][N:8]([CH3:10])[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 272414tert-Butyl hydroxy(methyl)carbamate

Product 1

HCID 86628343Tert-butyl 2-(3-hydroxypropoxy)ethoxy(methyl)carbamateYield 72%

Reagents, catalysts & solvents 2

HCID 82050Lithium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-Boc-N-methyl hydroxylamine (132 mg, 0.898 mmol), 2-(2-chloroethoxy)ethanol (168 mg, 1.35 mmol), K2CO3 (372 mg, 2.69 mmol) and LiBr (2 mg, 0.018 mmol) in DMF (3 mL) was heated at 100° C. and stirred for 16 h. The resulting mixture was cooled down to room temperature and filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography using 50% EtOAc/hexanes as eluent to afford the desired product as colorless oil (152 mg, 0.647 mmol, 72%). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.45 (s, 9H), 2.68 (br s, 1H), 3.08 (s, 3H), 3.57-3.60 (m, 2H), 3.66-3.72 (m, 4H), 3.96-3.99 (m, 2H).

Workup

  1. temperatureThe resulting mixture was cooled down to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-1c2f528da6d142729145a630b6776abc
Source dataset
uspto-grants-2011_08
Patent number
US07998486B2

Reaction notes

Loading…