Tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate → tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253717Notes

Reaction equation

[O:1]=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH:4]=[CH:3]1>CO.[Pd]>[O:1]=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (15.09 mmol, 1.0 eq.) in MeOH (40 ml) was degassed with argon for 15 min and then Pd—C (1.0 g) was added. The reaction mixture was stirred under H2 balloon pressure at 25° C. for 16 h. The mixture was filtered through celite and filtrate concentrated to give the desired product as a light yellow sticky solid. Yield: >99%

Workup

filtrationThe mixture was filtered through celite and filtrate
concentrationconcentrated

Sources & evidence

ORD record: ord-a619d205099e41ea96b34ac98e928a9d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455475B2

Reaction notes

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