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Water → (3-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenyl)methanol

HRID 2407249
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HRID 2407249 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C@@H:18]3[O:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[O:20][CH2:19]3)=O)[CH2:11]2)[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20][CH2:19][C@@H:18]1[CH2:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:10]([C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)[CH2:11]1
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6

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HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68489387(R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl ester

생성물 1

HCID 68486833(3-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenyl)methanol수율 7%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

((R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl ester (54 mg, 0.147 mmol) was dissolved in dry THF (4 ml) and cooled to 0° C. LiAlH4 (26 mg, 0.680 mmol) was added and the mixture was stirred at RT for 2 h. Water (1 ml), 1 M NaOH (1 ml) and again water (1 ml) were added slowly. The mixture was filtered through Celite and evaporated. Flash chromatography, using a gradient of heptane/EtOAc, gave 3.5 mg of the title compound.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

출처 및 근거

ORD 기록
ord-18ec6ce9dd654b9da018dd3a2fd46e0d
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809536B2

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