Trimethylsilyldiazomethane → Cyclopentanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester

HRID 1696178Notes

Reaction equation

HRID 1696178 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>CO.CCCCCC>[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acid

Product 1

HCID 22997550Cyclopentanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (2.29 g) in methanol (10 mL) was added dropwise 2M trimethylsilyldiazomethane solution in hexane (11.9 mL) under ice-cooling. The reaction mixture was concentrated, and to the residue was added hexane. The precipitated crystals were collected by filtration, and the filtrate was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=9/1 to 7/3). The product and the crystals obtained above were combined to give methyl 1-(tert-butoxycarbonylamino)-cyclopentane-carboxylate (2.49 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionto the residue was added hexane
  4. filtrationThe precipitated crystals were collected by filtration
  5. customthe filtrate was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=9/1 to 7/3)
  6. customThe product and the crystals obtained

Sources & evidence

ORD record
ord-d432759220d746fc8c98e2f1b37736f3
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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