HCID 54925194, compound → HCID 66593196, compound

HRID 1092336Notes

Reaction equation

HRID 1092336 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1)=O)[CH2:8]2>C1COCC1>[CH:3]12[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]([CH2:10]3)[CH:2]1[NH:11][CH2:12][C:14]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:9]2

Participants

3

Reactant 1

HCID 54925194HCID 54925194, compound

Product 1

HCID 66593196HCID 66593196, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-amino-cyclopentanecarboxylic acid adamantan-2-ylamide (220 mg) in THF (10 mL) was added borane-THF complex (4.65 mL) under argon. The mixture was then heated to reflux for 12 hours. It was then cooled and quenched with methanol (1 mL) to give a clear solution that was concentrated in vacuo. The residue was taken up in water, basified with 1 M NaOH and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography using 0.5% NH4OH in ethyl acetate as an eluent to give adamantan-2-yl-(1-amino-cyclopentylmethyl)-amine as a colorless semisolid (155 mg). MS (ESI): 249.3 (MH+).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 12 hours
  3. temperatureIt was then cooled
  4. customquenched with methanol (1 mL)
  5. customto give a clear solution that
  6. concentrationwas concentrated in vacuo
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2f9c0cf57c7d49dea17edcb59ac693e8
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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