Triphenylphosphine → 4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1993656Notes

Reaction equation

N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[N:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([O:22][C:20]2[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([CH3:15])[N:21]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 22 °C

Procedure

Add diisopropyl azodicarboxylate (3.0 mL, 15.5 mmol) dropwise to a cold mixture of 6-methyl-5-nitro-pyridin-2-ol (1.54 g, 10.0 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.05 g, 10.0 mmol), and triphenylphosphine (4.02 g, 15.3 mmol) in THF (25 mL) at 0° C. After addition is complete, remove cooling bath and stir the reaction mixture at 22° C. overnight. Concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to provide 4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil (2.69 g, 80% yield). MS(ES): m/z=338.2 [M+H].

Workup

additionAfter addition
customremove
temperaturecooling bath
concentrationConcentrate under reduced pressure
washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

Sources & evidence

ORD record: ord-8e6c4b8f165247ad9427c068060f673a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652015B2

Reaction notes

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