Acetic Acid → HCID 22251146, compound

HRID 890512Notes

Reaction equation

[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=O)[CH2:3]1)[CH2:9]2.[NH2:13][CH2:14][C:15]([N:17]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CN(C=O)C.ClCCCl>[CH:24]1([N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15](=[O:16])[CH2:14][NH:13][CH:5]2[CH:4]3[CH2:10][CH:8]4[CH2:9][C:2]([OH:1])([CH2:11][CH:6]2[CH2:7]4)[CH2:3]3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-hydroxy-2-adamantanone (80 mg, 0.48 mmol) in a mixed solvent of 1,2-dichloroethane and DMF (6 mL and 0.5 mL, respectively) at room temperature was added compound 2-amino-N-cyclohexyl-N-phenylacetamide (92 mg, 0.40 mmol). The reaction mixture was stirred for 15 minutes before cooling to 0° C. Sodium triacetoxyborohydride (128 mg, 0.60 mmol) was slowly added, followed by addition of glacial acetic acid (22 μL, 0.40 mmol). The reaction mixture was allowed to warm to room temperature, and then stirred for 24 hours. Concentration under reduced pressure, and purification on silica gel (5% methanol/dichloromethane) afforded N-cyclohexyl-2-[(5-hydroxyadamantan-2-yl)amino]-N-phenylacetamide CVT-6441 (90 mg, 60% yield). (M+1)=383.24.

Workup

temperatureto warm to room temperature
stirringstirred for 24 hours
concentrationConcentration
customunder reduced pressure, and purification on silica gel (5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-68e2f2a29d9c42f0bc13a4641e9a6f8c
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995285B2

Reaction notes

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