4-(1-Bromo-1-phenyl-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester → HCID 67046508, compound

HRID 606754Notes

Reaction equation

C[Sn](C)(C)[C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:8]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26](=[C:29](Br)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH2:25][C:26](=[C:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:3]2[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:8]=2)[CH2:27][CH2:28]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-trimethylstannyl-5-carboxyethylpyridine (0.298 g, 0.949 mmol) and 4-(1-bromo-1-phenyl-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.334 mL, 0.949 mmol) in dry THF (5 mL) was degassed with a stream of Ar bubbles for 10 min. To this solution was added bis(triphenylphosphine)palladium dichloride (0.033 g, 0.047 mmol) and then the reaction vessel was sealed and the mixture was heated at 90° C. (oil bath temperature) for 16 h. The cooled mixture was then evaporated to dryness and the residue chromatographed (SiO2/hexane-EtOAc, 7:3) to give the title compound (0.294 g, 73%) as a clear yellow oil:

Workup

customwas degassed with a stream of Ar bubbles for 10 min
customthe reaction vessel was sealed
customThe cooled mixture was then evaporated to dryness
customthe residue chromatographed (SiO2/hexane-EtOAc, 7:3)

Sources & evidence

ORD record: ord-ecb7b8602b964cbeb02173451bec8868
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915283B2

Reaction notes

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