Benzyl Bromide → Methyl 2,2-Dibenzyl-3-[4-(4-chlorophenyl)-4-fluoropiperidin-1-yl]propionate

HRID 537208Notes

Reaction equation

HRID 537208 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:20])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([C:15]([CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)([CH2:14][N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([F:20])[CH2:13][CH2:12]1)[C:16]([O:18][CH3:19])=[O:17])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 67462732Methyl 3-[4-(4-Chlorophenyl)-4-fluoropiperidin-1-yl]propionate

Product 1

HCID 67468586Methyl 2,2-Dibenzyl-3-[4-(4-chlorophenyl)-4-fluoropiperidin-1-yl]propionateYield 38%

Procedure

This compound was prepared from methyl 3-[4-(4-chlorophenyl)-4-fluoropiperidin-1-yl]propionate and 2.5 equivalents of both lithium hexamethyldisilazide and benzyl bromide as described in Step 2 of Example 4 in 38% yield.

Sources & evidence

ORD record
ord-03cfaf26f42f40ce838df5ba7d75bb59
Source dataset
uspto-grants-2014_10
Patent number
US08859777B2

Reaction notes

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