Dimethylformamide → HCID 18718010, compound

HRID 1937139Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1CCC[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.[CH:23]([Li])([CH2:25][CH3:26])[CH3:24].CN(C)C=[O:31]>>[CH:24]([C@@H:23]1[CH2:25][CH2:26][CH2:10][C@@H:9]([CH3:14])[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:31]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8037N,N,N',N'-Tetramethylethylenediamine

HCID 643491HCID 643491, compound

HCID 178418400CID 53628100

Product 1

HCID 18718010HCID 18718010, compoundYield 70%

Procedure

Similarly to Referential example 2, 2.10 g(10.5 mmol) of (R)-N-tert-butoxycarbonyl-2-methylpiperidine were reacted with 1.59 ml(1 equivalent) of N,N,N′,N′-tetramethylethylenediamine, 111.1 ml (1.1 equivalent) of sec-butyllithium(1.04M) and 1.22 ml(1.5 equivalents) of N,N-dimethylformamide to obtain 1.67 g of (2S,6R)-tert-butyl 2-formyl-6-methyl-1-piperidinecarboxylate(yield 70%).

Sources & evidence

ORD record: ord-713d55bcddb847cabf45643a8fee9d69
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392059B1

Reaction notes

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