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

HRID 526173
Notes
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Reaction equation

HRID 526173 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-4b5d3a000b594e9892a2c6079212c6a3
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09345709B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes