1-N-Boc-4-Piperidinecarboxylic acid methyl ester → 1-(1,1-Dimethylethyl) 4-methyl 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

HRID 1901080Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[CH:4]1[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.C([N-][CH:22]([CH3:24])[CH3:23])(C)C.[Li+]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1([CH2:8][C:9]2[CH:4]=[CH:5][CH:6]=[CH:24][C:22]=2[CH3:23])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:6][CH2:5]1

Participants

Reactant 2

HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl ester

HCID 2724682Lithium diisopropylamide

Product 1

HCID 537754431-(1,1-Dimethylethyl) 4-methyl 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

Procedure

N-t-butoxycarbonyl isonipecotic acid methyl ester was transformed utilizing the alkylation procedure as described in Example 1, Step 3 substituting lithium diisopropylamide as the base to afford the product as a yellow syrup.

Sources & evidence

ORD record: ord-67a1997ccb744cdfa71453a4fdff2959
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576313

Reaction notes

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