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Citric Acid → 4-[2-(5-Bromo-2-chloropyridin-4-yl)-1-hydroxy-ethyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 533116
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HRID 533116 반응식
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:26])[CH2:17][C:18]2[C:23]([Br:24])=[CH:22][N:21]=[C:20]([Cl:25])[CH:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13]([CH:16]([OH:26])[CH2:17][C:18]2[C:23]([Br:24])=[CH:22][N:21]=[C:20]([Cl:25])[CH:19]=2)[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
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참가 물질

6

반응물 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 866748944-[2-(5-Bromo-2-chloropyridin-4-yl)acetyl]piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 866748964-[2-(5-Bromo-2-chloropyridin-4-yl)-1-hydroxy-ethyl]piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

Sodium borohydride (240 mg) is added to an ice-cooled solution of 4-[2-(5-bromo-2-chloro-pyridin-4-yl)-acetyl]-piperidine-1-carboxylic acid tert-butyl ester (1.65 g) in a mixture of tetrahydrofuran (40 mL) and water (10 mL). The resulting mixture is stirred for 0.5 h at room temperature. 2 N Aqueous citric acid is added and the mixture is extracted with ethyl acetate. The combined extracts are washed with aqueous NaHCO3 solution and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 65:35) to give the title compound. LC (method 3): tR=1.48 min; Mass spectrum (ESI+): m/z=419, 421 [M+H]+.

후처리

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe combined extracts are washed with aqueous NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 65:35)

출처 및 근거

ORD 기록
ord-ec30c3f53dad4536bcb8b0f8e3ba92f5
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853239B2

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