Aluminium lithium hydride → 3-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine

HRID 2084613

반응식

HRID 2084613 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 227338424-(4-Fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one

생성물 1

HCID 46913-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, 0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.

후처리

  1. temperaturemaintaining the temperature below 25° C
  2. customquenched first of all with water (0.16 ml)
  3. stirringThe reaction mixture was stirred for 0.5 hours
  4. customthe precipitation
  5. additiondiluted with dichloromethane (30 ml)
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-fb0e71c853f743018e8c5ddad34674a8
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716985B2

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