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Triphenylphosphine → tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylate

HRID 2178894
Notes
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Reaction equation

HRID 2178894 reaction equation
[N+:1]([C:4]1C=CNN=1)([O-:3])=[O:2].O[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:42]([C:50](OC(C)C)=O)=[N:43][C:44](OC(C)C)=O>C1COCC1>[N+:1]([C:4]1[CH:50]=[N:42][N:43]([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)[CH:44]=1)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178526745HCID 178526745, compound

Product 1

HCID 56777238tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of nitropyrazole (3.0 g, 25 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (6.0 g, 30 mmol) and triphenylphosphine (7.9 g, 30 mmol) in THF (200 mL) at room temperature was added diisopropyl azodicarboxylate (6.0 g, 30 mmol) and the reaction mixture was stirred for 16 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, hexanes/ethyl acetate) to provide the desired product (4.2 g, 57%) as a white solid:

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-3baf36a7d7f242aaa91834ddd97707fb
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067937B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes