8-Benzyl-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester → Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate

HRID 1193054Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11](CC3C=CC=CC=3)[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 8-benzyl-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (1.34 g, 4.44 mmol) and wet Pd(OH)2/C (20 wt %, 938 mg) in EtOH (30 mL) was shaken under 60 psi atmosphere of H2 for 2 days at 50° C. The reaction mixture was filtered and concentrated to give title compound (1.0 g, 94%). MS (ESI) mass calcd. for C11H20N2O2, 212.29; m/z found, 213.2 [M+H]+. 1H NMR (CDCl3): 4.32-4.0 (m, 1H), 3.93-3.17 (m, 5H), 3.10-2.70 (m, 3H), 1.98-1.67 (m, 2H), 1.56-1.36 (m, 9H).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-261aa9d658024fd194b419b26c3022d1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680275B2

Reaction notes

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