Win 35428 → (1R,2S,3S)-2-Hydroxymethyl-3-(4-fluorophenyl)tropane

HRID 742316

반응식

HRID 742316 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C@H:11]1[C@@H:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][C@H:15]2[N:25]([CH3:26])[C@@H:12]1[CH2:13][CH2:14]2)(OC)=[O:8]>C(OCC)C>[OH:8][CH2:7][C@H:11]1[C@@H:17]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:16][C@H:15]2[N:25]([CH3:26])[C@@H:12]1[CH2:13][CH2:14]2

참가 물질

4

반응물 2

HCID 105056Win 35428HCID 21226445Aluminium lithium hydride

생성물 1

HCID 10514771(1R,2S,3S)-2-Hydroxymethyl-3-(4-fluorophenyl)tropane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a suspension of lithium aluminum hydride (0.8 g, 21 mmol) in diethyl ether (30 ml), at room temperature, was slowly added a solution of (1R,2S,3S)-2-carbomethoxy-3-(4-fluorophenyl)tropane (5 g, 18 mmol) in 100 ml diethyl ether. The reaction completes after stirring for 10 minutes and was quenched by addition of 0.8 ml water, 0.8 ml sodium hydroxide (15%) and 2 ml water. The aluminum salts were removed by filtration and the solvent was removed in vacuo leaving an oil. The title compound precipitates upon trituration with pentane as white crystals, m.p. 79°-800° C.

후처리

  1. customwas quenched by addition of 0.8 ml water, 0.8 ml sodium hydroxide (15%) and 2 ml water
  2. customThe aluminum salts were removed by filtration
  3. customthe solvent was removed in vacuo
  4. customleaving an oil
  5. customThe title compound precipitates upon trituration with pentane as white crystals, m.p. 79°-800° C.

출처 및 근거

ORD 기록
ord-2e92218d1c4e40039e66613fcec80af7
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554626

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