8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → HCID 86699010, compound

HRID 1520028Notes

Reaction equation

HRID 1520028 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:9][N:10]1[CH:14]2[CH2:15][CH:16](O)[CH2:17][CH:11]1[CH2:12][CH2:13]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>CN(C=O)C>[CH3:9][N:10]1[CH:14]2[CH2:13][CH2:12][CH:11]1[CH2:17][CH:16]([N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[CH2:15]2

Participants

6

Reactant 4

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 86699010HCID 86699010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Nitro-1H-pyrazole (10 g, 88.4 mmol) in DGM:DMF (3:1, 400 mL) were added Tropine (12.5 g, 88.4 mmol, 1 eq.), triphenyl phosphine (69.5 g, 265 mmol), followed by di-tert-butyl azodicarboxylate (61 g, 265 mmol) portionwise at 10-15° C. The reaction mixture was stirred at RT for 4 days. It was then concentrated under reduced pressure. The crude was purified by flash chromatography on silica (PetEther/EtOAc) to give the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.92 (s, 1H), 8.31 (s, 1H), 4.92-4.86 (m, 1H), 3.99 (m, 2H), 2.66-2.56 (m, 5H), 2.26-2.17 (m, 4H), 2.06-2.01 (m, 2H).

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. customThe crude was purified by flash chromatography on silica (PetEther/EtOAc)

Sources & evidence

ORD record
ord-a1a7081826e44e26b4c6aaa633cce9a4
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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