HCID 178501330, compound → HCID 178501328, compound

HRID 409483Notes

Reaction equation

HRID 409483 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@H:7]([O:9]CC2C=CC=CC=2)[CH2:6]1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@H:7]([OH:9])[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 178501330HCID 178501330, compound

Product 1

HCID 178501328HCID 178501328, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (730 mg, 3.32 mmol) as a 0.05 M solution in MeOH is pumped through the H-Cube™ flow hydrogenator fitted with a 10 mol % Pd/C catalyst cartridge heated to 40° C. at 10 bar. The flow rate was set at 1 ml/min. The solvent is removed under reduced pressure to give trans 3-hydroxy-cyclobutanecarboxylic acid methyl ester (400 mg, 92.7%); TLC (hexane/AcOEt, 1:1) Rf 0.38.

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-3632f85545004e06beea8e957bf4e265
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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