Trimethylsilyldiazomethane → 1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate

HRID 901462Notes

Reaction equation

HRID 901462 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:19]>CO.CCCCCC>[CH3:19][O:16][C:15]([CH:9]1[CH2:10][C:11](=[O:14])[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:17]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 10857681(2S)-1-[(tert-butoxy)carbonyl]-4-oxopiperidine-2-carboxylic acid

Product 1

HCID 104002141-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To (2S)-4-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.52 g, 2.15 mmol) in methanol (10 mL), 2 M solution of TMS-diazomethane (2 mL, 4 mmol) in hexane was added and stirred at room temperature for 15 min. The reaction solvent was removed and the methyl ester product obtained (4-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester) was used as such for the next reaction (0.55 g, 100%): MS (ESPOS): 258 [M+H]+; 1H NMR (300 MHz, CD3OD) δ 5.13, 4.86 (bs, 1), 4.02-4.11 (m, 1), 3.73 (s, 3), 3.67-3.72 (m, 1), 2.78 (d, J=4.2 Hz, 2), 2.51 (bs, 2), 1.46 (bs, 9).

Workup

  1. customThe reaction solvent was removed

Sources & evidence

ORD record
ord-7d6326beb96d469d93854eadb0e7d4fa
Source dataset
uspto-grants-2008_04
Patent number
US07361743B2

Reaction notes

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