Triphenylphosphine → 4-[3-(4-Methoxycarbonyl-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 220896노트

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HRID 220896 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24](O)=[C:23]([CH3:28])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:17][C:24]2[CH:25]=[CH:26][C:21]([C:20]([O:19][CH3:18])=[O:29])=[CH:22][C:23]=2[CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylateHCID 5462977Diethyl azodicarboxylateHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

생성물 1

HCID 575553354-[3-(4-Methoxycarbonyl-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic Acid Tert-butyl Ester수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

4-(3-Hydroxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester from Example E68.1 (400 mg, 1.64 mmol) and 4-hydroxy-3-methyl-benzoic acid methyl ester from Example E29 (274 mg, 1.64 mmol) were dissolved in THF (30 ml) and cooled down to 0° C. Polymer-supported triphenyl-phosphine (1.7 g, 2.46 mmol) then DEAD (0.387 ml, 2.46 mmol) were added and the mixture was heated at re-flux for 20 h. The resin was filtered off, washed with EtOAc and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAC:80% cyclohexane) to yield the title compound (340 mg, 53%).

후처리

  1. temperaturethe mixture was heated at re-flux for 20 h
  2. filtrationThe resin was filtered off
  3. washwashed with EtOAc
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAC:80% cyclohexane)

출처 및 근거

ORD 기록
ord-c5feb9ef99184824b65ed5daff4dd011
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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