tert-Butyl [3-(benzyloxy)cyclobutyl]carbamate → tert-Butyl (3-hydroxycyclobutyl)carbamate

HRID 2112092Notes

Reaction equation

C([O:8][CH:9]1[CH2:12][CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[OH:8][CH:9]1[CH2:10][CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:12]1

Participants

Conditions

Temperature: 45 °C

Procedure

2.77 g (10 mmol) tert.butyl (3-benzyloxy-cyclobutyl)-carbamate are suspended in 100 ml of methanol and combined with 200 mg palladium hydroxide. The reaction mixture is stirred for 5 h at 45° C. and 45 bar H2 pressure. Then the catalyst is filtered off and the solvent is eliminated in vacuo. The residue is taken up in chloroform and washed three times with aqueous sodium hydrogen carbonate solution. The organic phase is dried with magnesium sulphate and the solvent is eliminated in vacuo.

Workup

filtrationThen the catalyst is filtered off
washwashed three times with aqueous sodium hydrogen carbonate solution
dry with materialThe organic phase is dried with magnesium sulphate

Sources & evidence

ORD record: ord-2ce3e629d74f48249c2bb4dd59c50ac9
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521457B2

Reaction notes

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