Water → HCID 67083057, compound

HRID 42153Notes

Reaction equation

[Cl-].[Ca+2].[Cl-].O.[N+:5]([C:8]1[CH:9]=[C:10]([CH:32]=[CH:33][CH:34]=1)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:15][N:14]=1)([O-])=O>C(O)C.[Zn]>[NH2:5][C:8]1[CH:9]=[C:10]([CH:32]=[CH:33][CH:34]=1)[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:15][N:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of zinc powder (553 mg, 8.46 mmol) and calcium chloride (16 mg, 0.144 mmol) in ethanol (2.6 mL)-water (0.6 mL) was warmed to 90° C. followed by the addition of a solution of tert-butyl 4-[2-(3-nitrophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 30) (97 mg, 0.23 mmol) in ethanol (2 mL). The mixture was stirred at 90° C. for 1.5 hours, allowed to cool to room temperature and filtered through Celite pad. The filtrate was extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1→100/2) to give the title compound (84 mg, yield 94%).

Workup

temperatureto cool to room temperature
filtrationfiltered through Celite pad
extractionThe filtrate was extracted with ethyl acetate
washThe organic layer was washed sequentially with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1→100/2)

Sources & evidence

ORD record: ord-6e5bb8bf72c447a0bc99407fc028280d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536176B2

Reaction notes

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