HCID 59437178, compound → 4-(2-(1-Adamantylmethylamino)-1-hydroxyethyl)cyclohexanol

HRID 75152Notes

Reaction equation

[C:1]12([CH2:11][NH:12][CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[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>[C:1]12([CH2:11][NH:12][CH2:13][CH:14]([CH:16]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]3)[OH:15])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-((1-adamantylmethyl)amino)-1-hydroxyethyl)phenol (0.3 g, 1 mmol) in MeOH (10 mL) was added PtO2 (60 mg). The mixture was stirred under hydrogen (50 psi) at 60° C. for 2 d. The solvent was removed and purified by preparative TLC to give 4-(2-(1-adamantylmethylamino)-1-hydroxyethyl)cyclohexanol (100 mg, 32%). 1H NMR: (400 MHZ, CDCl3) δ=0.90-1.40 (m, 5H), 1.46 (m, 6H), 1.50-1.65 (m, 6H), 1.66-1.82 (m, 2H), 1.92 (m, 3H), 2.25 (m, 2H), 3.30 (m, 5H), 4.41 (m, 1H).

Workup

customThe solvent was removed
custompurified by preparative TLC

Sources & evidence

ORD record: ord-46a54235c9a94e738d5972981a7f37f0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835426B2

Reaction notes

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