Piperidine → 2-Admantyl-4-methyl-5-nitrophenol

HRID 73994Notes

Reaction equation

HRID 73994 reaction equation
C(=O)(OCC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([CH3:12])=[CH:5][C:4]=1[CH:13]1[CH:20]2[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:22][CH:14]1[CH2:15]3)[CH2:19]2.N1CCCCC1>C(Cl)Cl>[CH:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH:13]1[C:4]1[CH:5]=[C:6]([CH3:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[OH:2])[CH2:22]2

Participants

4

Reactant 2

HCID 8082PiperidineHCID 666862102-Admantyl-4-methyl-5-nitrophenyl ethyl carbonate

Product 1

HCID 666858672-Admantyl-4-methyl-5-nitrophenolYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-admantyl-4-methyl-5-nitrophenyl ethyl carbonate (378 mg, 1.05 mmol) in CH2Cl2 (5 mL) was added piperidine (1.0 mL). The solution was stirred at room temperature for 1 h, adsorbed onto silica gel under reduced pressure and purified by flash chromatography on silica gel (0-15%, EtOAc-Hexanes) to provide 2-admantyl-4-methyl-5-nitrophenol (231 mg, 77%).

Workup

  1. custompurified by flash chromatography on silica gel (0-15%, EtOAc-Hexanes)

Sources & evidence

ORD record
ord-21ba1d3bd4644cc794a67010f0c4b520
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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