Ethyl Acetate → HCID 68862824, compound

HRID 2110828Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=O)=[CH:4][CH:3]=1.B.O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][CH2:8][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(N-(4-chlorobenzyl)aminocarbonyl)-1-t-butoxycarbonylpiperidine (1.76 g, 5.0 mmol) in dry tetrahydrofuran (20 mL) stirring under argon at room temperature, was added borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 20 mL, 20 mmol). The resulting solution was heated to 80° C. for 16 h before cooling to 0° C. Saturated aqueous ammonium chloride (20 mL) was added, and the resulting mixture was stirred for 30 min before extraction with ethyl acetate (25 mL three times). The combined extracts were dried (anhydrous sodium sulfate) and evaporated under vacuum to obtain a gum, which was purified by column chromatography (silica gel, 100% ethyl acetate) to provide 4-(N-(4-chlorobenzyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.37 g, 81% yield) as a white solid.

Workup

temperaturebefore cooling to 0° C
dry with materialThe combined extracts were dried (anhydrous sodium sulfate)
customevaporated under vacuum
customto obtain a gum, which
customwas purified by column chromatography (silica gel, 100% ethyl acetate)

Sources & evidence

ORD record: ord-7a54cac2b2924e8ba704cefed162947e
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517991B2

Reaction notes

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