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Triphenylphosphine → Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate

HRID 1787899
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HRID 1787899 반응식
[CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:14])[CH:5]=1)([CH3:3])[CH3:2].O[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(Cl)Cl>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][CH2:22][CH:17]([CH2:16][O:14][C:6]2[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=[CH:12][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]
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참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 59745620Methyl 4-Isopropyl-2-hydroxybenzoate

생성물 1

HCID 68573359Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate수율 43%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

실험 절차

The methyl 4-isopropyl-2-hydroxybenzoate (4.4 g, 22.7 mmol) was dissolved in THF (100 mL). Then 3-(hydroxy-methyl)-1-tert-butoxycarbonylpiperidine (4.88 g, 22.7 mmol) and triphenylphosphine (7.14 g, 27.24 mmol) were added. The mixture was placed in an ice bath, and then diisopropyl azodicarboxylate (4.59 g, 22.7 mmol) in methylene chloride (15 mL) was added dropwise. The reaction mixture was allowed to warm gradually to room temperature. After 16 h, the solvent was removed under vacuum. The solid residue was subjected directly to flash chromatography on silica (0 to 30% EtOAc in hexane gradient), giving the title compound (3.34 g, 43% yield) as an oil.

후처리

  1. customThe mixture was placed in an ice bath
  2. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-f3d29e400cd341f0b5639776912b6bd4
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07511066B2

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