2-((1R,2S)-2-((benzyloxy)methyl)cyclopropyl)acetic acid → 2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetic acid

HRID 2202246Notes

Reaction equation

HRID 2202246 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:12][C@@H:11]1[CH2:13][C:14]([OH:16])=[O:15])C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][CH2:9][C@H:10]1[CH2:12][C@@H:11]1[CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 1186226992-((1R,2S)-2-((benzyloxy)methyl)cyclopropyl)acetic acid

Product 1

HCID 1186227692-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetic acidYield 103.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-((1R,2S)-2-((benzyloxy)methyl)cyclopropyl)acetic acid (884 mg, 4.01 mmol) in MeOH (20 mL) was stirred in the presence of 10% palladium-carbon (310 mg, 50%, wet) at room temperature for 3 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added toluene (about 20 mL), and the mixture was concentrated to give 2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetic acid (542 mg, 4.16 mmol, quant.) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added toluene (about 20 mL)
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-28401cd7618b4647ab7dc5ae90526c82
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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