HCID 8259841, compound → HCID 59437170, compound

HRID 75150Notes

Reaction equation

HRID 75150 reaction equation
[C:1]12([CH2:11][NH:12][CH2:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CO.O=[Pt]=O>[CH:16]1([C@H:14]([OH:15])[CH2:13][NH:12][CH2:11][C:1]23[CH2:2][CH:3]4[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]4)[CH2:10]2)[CH2:8]3)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 8259841HCID 8259841, compound

Product 1

HCID 59437170HCID 59437170, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (S)-2-((1-adamantylmethyl)amino)-1-phenylethanol (50 mg, 0.18 mmol) in dry CH3OH (5 mL) was added PtO2 (10 mg) as the catalyst. The mixture was stirred under hydrogen (55 psi) at 60-70° C. overnight. After filtration, the filtrate was evaporated to give a residue, which was purified by preparative TLC to give (S)-1-cyclohexyl-2-((1-adamantylmethyl)amino)ethanol (20 mg, 40%). 1H NMR (MeOD, 400 MHZ): δ=1.07-1.99 (m, 25H), 2.35-2.51 (q, 2H), 2.63 (t, 1H), 2.80 (d, 1H), 3.51 (m, 1H).

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated
  3. customto give a residue, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-510e3256959c42b0b15a6ee1faa19724
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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