Methanol → Ethyl 3-[4-(N-BOC-hydroxypiperidin-4-yl)phenyl]butyrate

HRID 265873Notes

Reaction equation

HRID 265873 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18](/[C:21](/[CH3:28])=[CH:22]\[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[OH:30]>[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=2)[CH2:10][CH:9]1[OH:30])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 67721045Ethyl 3-[4-(N-BOC-4-hydroxypiperidin-4-yl)phenyl]crotonate

Product 1

HCID 19034119Ethyl 3-[4-(N-BOC-hydroxypiperidin-4-yl)phenyl]butyrate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 12-1 (400 mg, 1.0 mmoles), 10% Pd/C (160 mg), and CH3OH (5 mL) was stirred at ambient temperature under a hydrogen atmosphere for 3.0 hours. The reaction mixture was filtered through a celite pad and the filtrate concentrated to give 12-2 as a yellow oil. Rf 0.33 (silica, 30% EtOAc/hexanes).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-452d160c4ea84adc9e7602413fe534c7
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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