2-Aminoadamantane hydrochloride → HCID 86653266, compound

HRID 72136Notes

Reaction equation

HRID 72136 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.C([O-])(O)=O.[Na+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20]>CC#N>[CH:10]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]([CH2:5]3)[CH:3]1[NH:2][C:19](=[O:20])[O:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)[CH2:9]2

Participants

5

Reactant 3

HCID 253312-Aminoadamantane hydrochlorideHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 86653266HCID 86653266, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 2-aminoadamantane HCl salt (1.24 g, 6.61 mmol) and powdered NaHCO3 (1.17 g, 13.9 mmol) in MeCN (40 mL) was added p-nitrophenyl chloroformate (1.40 g, 6.9 mmol). The mixture was stirred at rt for 1 d. The mixture was concentrated and the residue was taken up in ether (150 mL), washed with 5% aq HCl (50 mL) and brine (50 mL), and dried over MgSO4. Removal of the solvent left a white solid (1.81 g). Chromatography on a 40-g silica cartridge eluted with a 30-100% EtOAc in hexanes gradient to afford 4-nitrophenyl (2-adamantyl)carbamate (1.33 g, 63%).

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with 5% aq HCl (50 mL) and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft a white solid (1.81 g)
  6. washChromatography on a 40-g silica cartridge eluted with a 30-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-c314aae0c9f14ac1a967f330cdfe5b91
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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