HCID 178500382, compound → HCID 178500381, compound

HRID 2092003Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[C:4]([C@H:7]1[CH2:10][C@H:9]([O:11]CC2C=CC=CC=2)[CH2:8]1)([CH3:6])[CH3:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]([C@H:7]1[CH2:8][C@H:9]([OH:11])[CH2:10]1)([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of trans-2-(3-benzyloxy-cyclobutyl)-2-methyl-propionic acid methyl ester (70 mg, 0.26 mmol) as 0.05 M solution in MeOH is pumped through the H-Cube™ flow hydrogenator fitted with 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-2-(3-hydroxy-cyclobutyl)-2-methyl-propionic acid methyl ester (54 mg, quant.); TLC (hexane/AcOEt, 1:1) Rf 0.45, 1H NMR (400 MHz, chloroform-d) δ ppm 1.12 (s, 6H), 1.92-2.03 (m, 2H), 2.18-2.24 (m, 2H), 2.63-2.71 (m, 1H), 3.65 (s, 3H), 4.25-4.31 (m, 1H).

Workup

customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-a2dc7a0258704ee7a0fd545401bca618
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440682B2

Reaction notes

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