HCID 178462362, compound → HCID 178451083, compound

HRID 2202271Notes

Reaction equation

HRID 2202271 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][C@@H:8]1[CH2:11][C@H:10]([C:12]([O:14][C@H](C2C=CC=CC=2)C)=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:23])[CH2:7][C@@H:8]1[CH2:9][C@H:10]([C:12]([OH:14])=[O:13])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178462362HCID 178462362, compound

Product 1

HCID 178451083HCID 178451083, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-1-phenylethyl cis-3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylate (1.8 g, 5.65 mmol) and 10% palladium-carbon (0.602 g, 5.65 mmol, 50% wet) in MeOH (20 mL) was stirred at room temperature for 2 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to give cis-3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylic acid (1.200 g, 5.60 mmol, 99%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ1.43 (9H, s), 1.92-2.10 (2H, m), 2.29-2.48 (4H, m), 2.48-2.78 (1H, m), 2.93-3.16 (1H, m) (The peak derived from COOH was not observed).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-39aa782ac81b46df972328636efa7442
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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