HCID 13754447, compound → HCID 13754448, compound

HRID 2118836Notes

Reaction equation

HRID 2118836 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1([OH:25])[CH2:21][CH2:22][CH2:23][CH2:24]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 13754447HCID 13754447, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13754448HCID 13754448, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(t-butoxycarbonyl)-α-(1-hydroxycyclopentyl)glycine, benzyl ester (1.81 g, 4.98 mmoles) in 30 ml of absolute ethanol at 25° C. was treated with 0.4 g of 10% palladium on charcoal and hydrogen at one atmosphere for 2.5 hours. The catalyst was filtered and the solvent evaporated. Benzene was added and evaporated. Crystallization from isopropyl ether (first crop) and hexane (second crop) gave a total of 1.07 g of product, melting point 132°-134° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated
  3. additionBenzene was added
  4. customevaporated
  5. customCrystallization from isopropyl ether (first crop) and hexane (second crop)

Sources & evidence

ORD record
ord-b45d3e5b46a842a9ac0a71e7cfd565c3
Source dataset
uspto-grants-1987_07
Patent number
US04680388

Reaction notes

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