Benzyl succinimido carbonate → HCID 22994595, compound

HRID 1278786Notes

Reaction equation

HRID 1278786 reaction equation
[NH2:1][C:2]12[CH2:13][C:6]3([CH3:14])[CH2:7][C:8]([CH2:11][OH:12])([CH2:10][C:4]([CH3:15])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:16]([O:23][C:24](ON1C(=O)CCC1=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([O:23][C:24]([NH:1][C:2]12[CH2:13][C:6]3([CH3:14])[CH2:7][C:8]([CH2:11][OH:12])([CH2:10][C:4]([CH3:15])([CH2:5]3)[CH2:3]1)[CH2:9]2)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 9921196HCID 9921196, compound

Product 1

HCID 22994595HCID 22994595, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-amino-3,5-dimethyl-7-hydroxymethyl adamantane (60 mg) in THF (3 mL) was added N-(benzyloxycarbonyloxy)-succinimide (74 mg) and the mixture was stirred at room temperature overnight. THF was removed and the residue was dissolved in ethyl acetate. The solution was washed with water and brine. The product was purified by thin layer chromatography eluting with ethyl acetate and hexane (1:4, v/v) to give a white solid (80 mg). 1H NMR (DMSO-d6, ppm): 7.33 (in, 5 H, C6H5), 6.89 (brs, 1 H, NH), 4.94 (s, 2 H, OCH2), 4.32 (t, 1 H, OH, J=5.7 Hz), 3.04 (d, 2 H, CH2OH, J=5.7 Hz), 1.46 (dd, 6 H), 1.04 (dd, 6 H), 0.84 (s, 6 H, 2×CH3).

Workup

  1. customTHF was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water and brine
  4. customThe product was purified by thin layer chromatography
  5. washeluting with ethyl acetate and hexane (1:4, v/v)

Sources & evidence

ORD record
ord-c5f0c12493df47849129010f4e2d3b5f
Source dataset
uspto-grants-2002_09
Patent number
US06444702B1

Reaction notes

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