Methanol → 3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acid

HRID 2074298Notes

Reaction equation

[OH-].[Na+].C1COCC1.CO.C[O:11][C:12]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:17]=[CH:18][CH:19]=1)=[O:13]>CCOC(C)=O>[C:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][CH:22]([CH2:21][CH2:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:12]([OH:13])=[O:11])[CH2:23][CH2:24]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

Aqueous 1 M sodium hydroxide solution (196 ml) was added to a THF (200 ml)/methanol (50 ml) mixed solution of tert-butyl 4-{2-[3-(methoxycarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (45.4 g), followed by stirring at 60° C. for 2 hours. The organic solvent was evaporated under reduced pressure, and under ice cooling, 0.5 M hydrochloric acid (400 ml) was added to the residue. The reaction liquid was diluted with EtOAc, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 3-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}benzoic acid (43.5 g) was obtained.

Workup

customThe organic solvent was evaporated under reduced pressure
additionunder ice cooling, 0.5 M hydrochloric acid (400 ml) was added to the residue
customThe reaction liquid
washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-60b37790b07742a8b8a2b812428f4a25
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919495B2

Reaction notes

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