tert-Butanol → HCID 69094616, compound

HRID 69908Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C[C:19]1([C:34](O)=O)[CH2:24][CH2:23][CH2:22][N:21]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:20]1.CC[N:39]([CH2:42]C)CC.[CH3:44][C:45]([OH:48])([CH3:47])[CH3:46]>>[CH3:34][C:19]1([NH:39][C:42](=[O:8])[O:48][C:45]([CH3:47])([CH3:46])[CH3:44])[CH2:24][CH2:23][CH2:22][N:21]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:20]1

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 63136298HCID 63136298, compound

Product 1

HCID 69094616HCID 69094616, compound

Conditions

Temperature: 85 °C

Procedure

Diphenylphosphoryl azide (1.2 eq) was added to a mixture of 3-methyl 1-(3-nitropyridin-4-yl)piperidine-3-carboxylic acid (1 eq) and anhydrous tBuOH (0.3 M), followed shortly by Et3N (2 eq). The reaction flask was fitted with an air-cooled reflux condenser and bubble vent, then heated in an 85° C. oil bath for 3 days. The crude mixture was diluted with EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (10-20-40% EtOAc in hexanes) to give tert-butyl 3-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate. LC/MS (m/z): 337.2 (MH+).

Workup

customThe reaction flask was fitted with an air-cooled
temperaturereflux condenser
custombubble vent
additionThe crude mixture was diluted with EtOAc
washwashed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
dissolutionThe crude residue was dissolved in CH2Cl2
custompurified by flash chromatography (10-20-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-68d5b5c10a24416cb540700f00c4e1fb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822497B2

Reaction notes

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