Water → 1-[2-(4-Cyanophenyl)ethyl]-4-(4-hydroxymethylphenoxymethyl)piperidin-4-ol

HRID 967766노트

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HRID 967766 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+].O>C(O)C.O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:8]=1)#[N:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 222912951-[2-(4-Cyanophenyl)ethyl]-4-(4-formylphenoxymethyl)piperidin-4-ol

생성물 1

HCID 99691581-[2-(4-Cyanophenyl)ethyl]-4-(4-hydroxymethylphenoxymethyl)piperidin-4-ol수율 79.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

The compound (0.20 g) obtained in Step 1 was dissolved in a mixture of ethanol (3 mL) and tetrahydrofuran (2.75 mL) and to this solution was added sodium borohydride (0.016 g) under cooling with ice-water and the mixture was stirred at the same temperature for two hours under nitrogen atmosphere. After adding water (15 mL) and stirring, to the mixture was added salt until it was saturated, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (Chromatorex NH™) (eluent; ethyl acetate:methanol=99:1 to 9:1) to obtain the titled compound (0.16 g).

후처리

  1. stirringstirring, to the mixture
  2. additionwas added salt until it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (Chromatorex NH™) (eluent; ethyl acetate:methanol=99:1 to 9:1)

출처 및 근거

ORD 기록
ord-4f2eb161733649c29e5af72a0f020f30
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956046B2

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