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

HRID 1808268

Reaktionsgleichung

Reaktionsgleichung von HRID 1808268
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82050Lithium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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, 9 H), 2.68 (br s, 1 H), 3.08 (s, 3 H), 3.57-3.60 (m, 2 H), 3.66-3.72 (m, 4 H), 3.96-3.99 (m, 2 H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-07d5457fdc3c446a991750a4d4e50b29
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357777B2

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