(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-isopropylcyclopent-2-enecarboxylic acid → (1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acid

HRID 1044553Notes

Reaction equation

HRID 1044553 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH:17]([CH3:19])[CH3:18])([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C@:12]([CH:17]([CH3:19])[CH3:18])([C:14]([OH:16])=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 60122256(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-isopropylcyclopent-2-enecarboxylic acid

Product 1

HCID 60122293(1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1S,4S)-4-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopent-2-ene-1-carboxylic acid (9.78 g, 36.3 mmol) in ethanol (250 mL) was added 10% palladium on carbon (550 mg). The mixture was shaken under hydrogen at 55 psi overnight and filtered through celite. The filtrate was evaporated in vacuo to afford the title compound (9.45 g, 96%). MS calculated for C14H25NO4: (M+H)+ 272; found 172.1 (M-Boc+H)+.

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5e55a1913b474866a7234300028baab0
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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