Isopropenylacetylene → {(2S,4R)-1-{(1S)-4-Methyl-1-[4-(pentafluoroethyl)phenyl]pent-4-en-2-yn-1-yl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

HRID 1869760Notes

Reaction equation

HRID 1869760 reaction equation
[F:1][C:2]([F:15])([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].C[CH:17]([C@@H:21]1[CH2:26][CH2:25][NH:24][C@H:23]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:22]1)[C:18]([O-:20])=[O:19].[CH3:37][C:38]([C:40]#[CH:41])=[CH2:39]>>[CH3:39][C:38](=[CH2:37])[C:40]#[C:41][C@@H:11]([N:24]1[CH2:25][CH2:26][C@@H:21]([CH2:17][C:18]([OH:20])=[O:19])[CH2:22][C@H:23]1[C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=1)[C:10]1[CH:13]=[CH:14][C:7]([C:2]([F:15])([F:1])[C:3]([F:6])([F:5])[F:4])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 62323IsopropenylacetyleneHCID 579874184-(Perfluoroethyl)benzaldehydeHCID 86617999(+)-methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate

Product 1

HCID 57987447{(2S,4R)-1-{(1S)-4-Methyl-1-[4-(pentafluoroethyl)phenyl]pent-4-en-2-yn-1-yl}-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

Procedure

The title compound was prepared from the aldehyde from Step 2, methyl{(2S,4R)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Example 114, Step 1) and 2-methylbut-1-en-3-yne as described in Example 116. M/Z (ES+) 560 (MH+). 1H NMR (400 MHz, CDCl3): δ 1.33 (1H, dq, J 5.2, 13.4), 1.46 (1H, q, J 11.9), 1.75 (1H, d, J 10.6), 1.94 (1H, d, J 13.4), 1.98-2.05 (4H, m), 2.23-2.36 (2H, m), 2.43-2.54 (2H, m), 3.69 (1H, dd, J 2.6, 11.1), 4.60 (1H, s), 5.32 (1H, quintet, J 1.6), 5.4 (1H, s), 7.54 (2H, d, J 8.2), 7.62 (4H, br s), 7.67 (2H, d, J 8.2).

Sources & evidence

ORD record
ord-b5fe13b982284be6b52d517803e6908c
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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