Benzyl succinimido carbonate → HCID 22994595, compound

HRID 2053057Notes

Reaction equation

HRID 2053057 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 (m, 5H, C6H5), 6.89 (brs, 1H, NH), 4.94 (s, 2H, OCH2), 4.32 (t, 1H, OH, J=5.7 Hz), 3.04 (d, 2H, CH2OH, J=5.7 Hz), 1.46 (dd, 6H), 1.04 (dd, 6H), 0.84 (s, 6H, 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-9ff12235c4534fd1b4451e5c14385f76
Source dataset
uspto-grants-2008_02
Patent number
US07326730B2

Reaction notes

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