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

HRID 1808268

反応式

HRID 1808268 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82050Lithium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-07d5457fdc3c446a991750a4d4e50b29
出典データセット
uspto-grants-2013_01
特許番号
US08357777B2

関連ノート

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