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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 872197
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HRID 872197 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]
참가 물질실험 절차후처리출처 및 근거반응 노트

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 (0.24 g) is added to an ice-cold solution of 4-[2-(5-bromo-2-chloro-pyridin-4-yl)-acetyl]-piperidine-1-carboxylic acid tert-butyl ester (1.65 g) in tetrahydrofuran (40 mL) and water (10 mL). The resulting mixture is stirred for 0.5 h. 2 N aqueous citric acid solution is added and the mixture is extracted with ethyl acetate. The combined extracts are washed with aqueous NaHCO3 solution and brine, dried (MgSO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 65:35) to give the title compound. Mass spectrum (ESI+): m/z=419/421/423 (Cl+Br) [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 (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 65:35)

출처 및 근거

ORD 기록
ord-7490d6b2c5d6456caffdc5b1404a9dff
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975277B2

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