benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylate → (2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidine

HRID 2249679Notes

Reaction equation

HRID 2249679 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][CH:4]=[CH:5][C@@H:6]1[CH2:10][C@@H:9]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH2:8][N:7]1C(OCC1C=CC=CC=1)=O.[H][H]>C(O)C.[C].[Pd]>[CH2:12]([O:11][C@H:9]1[CH2:8][NH:7][C@H:6]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:26])[CH3:1])[CH2:10]1)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 86630055benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68984938(2R,4R)-4-isobutoxy-2-(4-methylpentyl)pyrrolidineYield 97.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 5.8 ml of ethanol is dissolved 0.29 g of benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylate. After adding 0.06 g of 5% palladium-carbon, the mixture is stirred at ambient temperature for 1.5 hours in a stream of hydrogen. The reaction mixture is filtered with Celite, and the solvent is distilled off from the filtrate under reduced pressure. Thus, 0.18 g of (2R,4R)-4-isobutoxy-2-(4-methylpentyl)-pyrrolidine is obtained as a yellow oily product.

Workup

  1. filtrationThe reaction mixture is filtered with Celite
  2. distillationthe solvent is distilled off from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-095370c973924051848badfe28e495d7
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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