Toluene → Methyl 3-[4-(3-Benzyloxyphenyl)-4-fluoro-3-methylpiperidin-1-yl]-2,2-dibenzylpropionate

HRID 537221Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([F:28])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:17][CH:16]2[CH3:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1COCC1.[C:52]1([CH3:58])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([F:28])[CH2:20][CH2:19][N:18]([CH2:21][C:22]([CH2:58][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:23]([O:25][CH3:26])=[O:24])[CH2:17][CH:16]2[CH3:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 5

HCID 1140Toluene

HCID 7498Benzyl Bromide

HCID 8028Tetrahydrofuran

HCID 2733832Lithium Hexamethyldisilazide

HCID 67464042Methyl 3-[4-(3-Benzyloxyphenyl)-4-fluoro-3-methylpiperidin-1-yl]propionate

Product 1

HCID 67461666Methyl 3-[4-(3-Benzyloxyphenyl)-4-fluoro-3-methylpiperidin-1-yl]-2,2-dibenzylpropionate

Procedure

This compound was prepared from methyl 3-[4-(3-benzyloxyphenyl)-4-fluoro-3-methylpiperidin-1-yl]propionate and 2.5 equivalents of both lithium hexamethyldisilazide and benzyl bromide as described in Step 2 of Example 4 with the exception that THF was used as the reaction solvent as opposed to toluene. The desired compound was obtained in 42% overall yield.

Sources & evidence

ORD record: ord-0a7be5818ade4f289e12873d74668795
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859777B2

Reaction notes

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