HCID 178501330, compound → HCID 178501328, compound

HRID 2091987Notes

Reaction equation

HRID 2091987 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 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (680 mg, 3.09 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 is set at 1 ml/min. The solvent is removed under reduced pressure to give trans 3-hydroxy-cyclobutanecarboxylic acid methyl ester (380 mg, 94.5%); TLC (hexane/AcOEt, 1:1) Rf 0.38, 1H NMR (400 MHz, chloroform-d) δ ppm 2.18-2.25 (m, 2H), 2.55-2.61 (m, 2H), 3.01-3.08 (m, 1H), 3.70 (s, 3H), 4.53-4.61 (m, 1H).

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-df6e2dba1a26462a9405f8179ec51dad
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

Loading…