Ammonium formate → 4-Tert-butyl 1-piperidin-4-yl 2-((pyridin-3-yloxy)methyl)piperazine-1,4-dicarboxylate

HRID 1487773Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][N:10]2[C:22]([O:24][CH:25]2[CH2:30][CH2:29][N:28](C(OCC3C=CC=CC=3)=O)[CH2:27][CH2:26]2)=[O:23])[CH:2]=1.C([O-])=O.[NH4+]>CCO.[OH-].[OH-].[Pd+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:12][CH2:11][N:10]2[C:22]([O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:23])[CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Palladium hydroxide on carbon (˜10% Pd, 84 mg, 0.06 mmol) was added to a mixture of 1-(1-(benzyloxycarbonyl)piperidin-4-yl) 4-tert-butyl 2-((pyridin-3-yloxy)methyl)piperazine-1,4-dicarboxylate (0.665 g, 1.20 mmol) and ammonium formate (0.151 g, 2.40 mmol) in EtOH (10 mL). The reaction mixture was heated to 70° C. for 2 h. Upon cooling to rt, the reaction mixture was filtered though Celite®, and the filtrate was concentrated under reduced pressure. This gave 0.5278 g of crude product. LC-MS: RT=4.50 min, [M+H]+=421.2.

Workup

temperatureUpon cooling to rt
filtrationthe reaction mixture was filtered though Celite®
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-3c136496bdb048eba7f2b5ffc0c867e7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428522B2

Reaction notes

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