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

HRID 1808268

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HRID 1808268 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 82050Lithium Bromide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-07d5457fdc3c446a991750a4d4e50b29
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357777B2

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