Reaktion #1956955

ord-376732b3025e466787239d5dca6a7987

Reaktionsgleichung

O=Cc1ccc(Cl)cc1
4-chlorobenzaldehyde
CC(C)CCBr
1-bromo-3-methylbutane
CC(C(=O)[O-])[C@@H]1CCN[C@H](c2ccc(C(F)(F)F)cc2)C1
piperidine
CC(C(=O)[O-])[C@@H]1CCN[C@H](c2ccc(C(F)(F)F)cc2)C1
(±)-Methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate
→
CC(C)CC[C@H](c1ccc(Cl)cc1)N1CC[C@@H](CC(=O)O)C[C@H]1c1ccc(C(F)(F)F)cc1
{(2S,4R)-1-[(1R)-1-(4-chlorophenyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Edukte

O=Cc1ccc(Cl)cc1
4-chlorobenzaldehyde
—
Grignard reagent
CC(C)CCBr
1-bromo-3-methylbutane
CC(C(=O)[O-])[C@@H]1CCN[C@H](c2ccc(C(F)(F)F)cc2)C1
piperidine
CC(C(=O)[O-])[C@@H]1CCN[C@H](c2ccc(C(F)(F)F)cc2)C1
(±)-Methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The compound was prepared analogously to Example 160 using the Grignard reagent derived from 1-bromo-3-methylbutane, starting with the chiral piperidine of Example 114 Step 1 and replacing 4-(trifluoromethyl)benzaldehyde with 4-chlorobenzaldehyde. M/Z (ES+) 482 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07638629B2uspto-grants-2009_12