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

HRID 868828Notes

Reaction equation

HRID 868828 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[N+:50]([C:53]1[CH:54]=[N:55][NH:56][CH:57]=1)([O-:52])=[O:51]>C1COCC1>[N+:50]([C:53]1[CH:54]=[N:55][N:56]([CH:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:57]=1)([O-:52])=[O:51]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 97268Di-tert-butyl azodicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 56777238tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylateYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Boc-4-hydroxy piperidine (2.6 g, 0.0132 mol), triphenylphosphine (4.1 g, 0.015 mol) and di-tert-butyl azodicarboxylate (3.9 g, 0.0172 mol) are added in portions to a solution of 4-nitro-1H-pyrazole (1.5 g, 0.0132 mol) in THF (40 ml) at 10-15° C. The reaction mixture is stirred at room temperature for 48 h. The mixture is evaporated in a rotary evaporator, and the crude material is chromatographed, giving 2.1 g of a white solid;

Workup

  1. customThe mixture is evaporated in a rotary evaporator
  2. customthe crude material is chromatographed

Sources & evidence

ORD record
ord-073fe50a50614ec3b89292f1482cdfb9
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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