Malonic Acid → 3-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]prop-2-ene-1-oic acid

HRID 520812Notes

Reaction equation

HRID 520812 reaction equation
C([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=O.[C:23](O)(=O)[CH2:24][C:25]([OH:27])=[O:26].N1CCCCC1>N1C=CC=CC=1>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([O:7][C:6]2[CH:21]=[CH:22][C:3]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:19])([CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 22632605tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylate

Product 1

HCID 900421133-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]prop-2-ene-1-oic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of t-Butyl 4-(4-formyl phenoxy)piperidine-1-carboxylate (50.2 grams, 0.164 moles, obtained in above step), malonic acid (50.6 grams, 0.486 moles) and piperidine (12.5 mL) in pyridine (250 mL) was stirred for 8 hours at 110° C. under nitrogen atmosphere.

Sources & evidence

ORD record
ord-20138aec10724831b047a0919b58f274
Source dataset
uspto-grants-2016_05
Patent number
US09328092B2

Reaction notes

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