8-((1R)-1-Phenyl-ethyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic Acid Tert-Butyl Ester → cis-3-Boc-3,8-diazabicyclo[4.2.0]octane

HRID 253177Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C@@H](C3C=CC=CC=3)C)[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C@@H:13]2[C@@H:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To the minor isomer product of Example 3E (2.4 g, 7.5 mmol) in 30 mL CH3OH was added 0.58 g of 20% Pd(OH)2/C (wet). This mixture was shaken under 60 psi of H2 for 16.5 h at 50° C. The mixture was filtered, concentrated to proved the title compound, suitable for use without further purification. MS (DCl/NH3) m/z 213 (M+H)+.

Workup

filtrationThe mixture was filtered
concentrationconcentrated
customsuitable for use without further purification

Sources & evidence

ORD record: ord-51a63d17c8834679bcaf5b704464d5ab
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872010B2

Reaction notes

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