Potassium Carbonate → HCID 25167162, compound

HRID 658818Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2,2,2-trifluoro-N-(2-(3-((1-hydroxycycloheptyl)ethynyl)phenoxy)ethyl)acetamide (1.07 g, 2.9 mmol) in MeOH (20 mL) was added saturated aqueous K2CO3 (ca. 10 mL). The reaction mixture was stirred vigorously and heated at 50° C. for 2 h. After removal of the volatiles by concentration under reduced pressure, the mixture was partitioned into EtOAc and water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (10% 7M NH3 in MeOH-EtOAc) gave 1-((3-(2-aminoethoxy)phenyl)ethynyl)cycloheptanol as a pale yellow solid. (Yield 0.70 g, 88%): 1H NMR (400 MHz, CDCl3) δ 7.19 (t, J=8.0 Hz, 1H), 7.01 (dt, J=8.0, 0.8 Hz, 1H), 6.95 (dd, J=2.8, 1.6 Hz, 1H), 6.85 (ddd, J=−8.4, 2.4, 1.2 Hz, 1H), 3.97 (t, J=4.8 Hz, 2H), 3.07 (br s, 2H), 2.08-2.13 (n4, 2H), 1.87-1.94 (m, 2H), 1.59-1.74 (m, 1H).

Workup

customAfter removal of the volatiles
concentrationby concentration under reduced pressure
customthe mixture was partitioned into EtOAc and water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customPurification by flash chromatography (10% 7M NH3 in MeOH-EtOAc)

Sources & evidence

ORD record: ord-30d1c169f11649fc8e895152e81886c9
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076516B2

Reaction notes

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