Triphenylphosphine → Methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoate

HRID 644188Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

The methyl 2-hydroxy-4-(methylthio)benzoate (4.00 g, 20.2 mmol) was dissolved in THF (300 mL). The solution was cooled to 0° C. and the N-Boc-4-hydroxypiperidine (4.07 g, 20.2 mmol) and triphenylphosphine (6.35 g, 24.2 mmol) were added, followed by diethyl azodicarboxylate (4.0 mL, 25.4 mmol). After 5 minutes, the reaction was allowed to warm to room temperature and left overnight. The reaction was concentrated in vacuo and the crude material was purified by flash column chromatography (about 500 g silica, 15% EtOAc/hexanes tthrough 20% EtOAc/hexanes) to give the desired product (7.185 g, 18.83 mmol, 93%).

Workup

temperatureto warm to room temperature
waitleft overnight
concentrationThe reaction was concentrated in vacuo
customthe crude material was purified by flash column chromatography (about 500 g silica, 15% EtOAc/hexanes tthrough 20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ff1e575cd93144db9a9fc6ec69a05f0c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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