Ethyl diazoacetate → ethyl N-(benzyloxycarbonyl)piperidin-4-ylmethoxyacetate

HRID 1900915Notes

Reaction equation

HRID 1900915 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N-]>C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+3].[Rh+3].ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 23370014ethyl N-(benzyloxycarbonyl)piperidin-4-ylmethoxyacetate

Reagents, catalysts & solvents 2

HCID 86657289Di-rhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 20, starting material step (a), N-benzyloxycarbonylpiperidine-4-methanol (2 g, preparation described in Turconi, M. et al (1989), European Patent Application No. 309422-A2), dirhodium tetraacetate (40 mg), dichloromethane (15 ml total) and ethyl diazoacetate (1.2 ml) were reacted to give ethyl N-(benzyloxycarbonyl)piperidin-4-ylmethoxyacetate (1.47 g) as a colourless oil: NMR Spectrum (DMSO-d6) 1.10 (2H, m), 1.20 (3H, t), 1.70 (3H, m), 2.80 (2H, m), 3.31 (2H, d), 4.00 (2H, m), 4.06 (2H, s), 4.12 (2H, q), 5.06 (2H, s), 7.35 (5H, m); Mass Spectrum m/Z 336 (M+H)+.

Workup

  1. custom2 g, preparation

Sources & evidence

ORD record
ord-5c9219b6a0cc4dbe8a98de5eabfb5191
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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