Trimethylsilyldiazomethane → tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 1913260Notes

Reaction equation

HRID 1913260 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1.CO>[CH3:2][O:23][C:22](=[O:24])[CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:14])[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acid

Product 1

HCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

At 0° C., TMSCHN2 (2.0 M in ether, 15 mL) was added dropwise to a mixture of 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid (6272 mg, 25.78 mmoL) in toluene (60 mL) and MeOH (60 mL). After stirring at room temperature for 1 h, the mixture was concentrated. The crude tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (Int-12a) was pure enough without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe crude tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (Int-12a) was pure enough without further purification

Sources & evidence

ORD record
ord-177033c838964100b81cc99115d96f0e
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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