Ammonia methanol → HCID 57608482, compound

HRID 2098510Notes

Reaction equation

HRID 2098510 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH:8]([OH:24])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[OH:23])[CH:10]=1)=O.N.CO>ClCCl>[NH2:5][CH2:6][CH2:7][CH:8]([C:9]1[CH:10]=[C:11]([C:15]#[C:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[OH:23])[CH:12]=[CH:13][CH:14]=1)[OH:24]

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 86628458HCID 86628458, compound

Product 1

HCID 57608482HCID 57608482, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection of 2,2,2-trifluoro-N-(3-hydroxy-3-(3-((2-hydroxycyclohexyl)ethynyl)phenyl)propyl)acetamide followed by flash chromatography (10% (7N NH3/MeOH)/dichloromethane) gave 2-((3-(3-amino-1-hydroxypropyl)phenyl)ethynyl)cyclohexanol as a light yellow glassy solid. Yield (0.402 g, 29%): 1H NMR (400 MHz, CDCl3) δ 7.44-7.46 (m, 1H), 7.21-7.31 (m, 3H), 4.92 (dd, J=8.8, 3.2 Hz, 1H), 3.47-3.56 (m, 1H), 3.05-3.12 (m, 1H), 3.01 (brs, 4H), 2.90-2.99 (m, 1H), 2.37-2.44 (m, 1H), 2.00-2.09 (m, 2H), 1.81-1.90 (m, 1H), 1.64-1.81 (m, 3H), 1.40-1.52 (m, 1H), 1.14-1.40 (m, 3H).

Sources & evidence

ORD record
ord-e2ec30da2de14430b8be0293968aa703
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

Loading…