Binap, (A+-)- → 1-Tert-butyl 4-ethyl 4-(2-methylenebutyl)piperidine-1,4-dicarboxylate

HRID 1848492Notes

Reaction equation

Br[C:2](=[CH2:22])[CH2:3][C:4]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([Zn][CH2:72][CH3:73])C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:22]=[C:2]([CH2:72][CH3:73])[CH2:3][C:4]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-tert-butyl 4-ethyl 4-(2-bromoallyl)piperidine-1,4-dicarboxylate (5.0 g, 13.3 mmol) in THF (80 mL) in a sealed tube was added BINAP (3.31 g, 5.32 mmol), diethylzinc (15.95 mL, 15.95 mmol) and Pd(OAc)2 (0.597 g, 2.66 mmol) and the resulting mixture was degassed and heated for 16 hours at 100° C. The reaction mixture was evaporated to remove solvent under reduced pressure and the crude product was purified by silica gel column chromatography (RediSep 220 g Gold column) using (0-30) % EtOAc/Hexanes as mobile phase and the title compound was isolated.

Workup

customthe resulting mixture was degassed
customThe reaction mixture was evaporated
customto remove solvent under reduced pressure
customthe crude product was purified by silica gel column chromatography (RediSep 220 g Gold column)

Sources & evidence

ORD record: ord-862812ba590d485f8ee484948924df14
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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