Potassium Carbonate → 2,2,2-trifluoro-N-(3-(3-(2-(1-hydroxycycloheptyl)ethyl)phenyl)propyl)acetamide

HRID 1021089Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][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:4].C([O-])([O-])=O.[K+].[K+]>>[F:1][C:2]([F:25])([F:26])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][C:17]2([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:10]=1)=[O:4]

Participants

Reactant 2

HCID 11430Potassium Carbonate

HCID 86628453HCID 86628453, compound

Product 1

HCID 866358542,2,2-trifluoro-N-(3-(3-(2-(1-hydroxycycloheptyl)ethyl)phenyl)propyl)acetamide

Procedure

Deprotection of 2,2,2-trifluoro-N-(3-(3-((1-hydroxycycloheptyl)ethynyl)phenyl)propyl)acetamide was conducted following the method used to prepare Example 2 except that 5 equivalents of K2CO3 were used and the reaction was stirred at room temperature overnight. Purification by flash chromatography (10% 7M NH3 in MeOH/CH2Cl2) gave 2,2,2-trifluoro-N-(3-(3-(2-(1-hydroxycycloheptyl)ethyl)phenyl)propyl)acetamide as a clear oil. Yield (0.635 g, 86%): 1H NMR (400 MHz, DMSO-d6) δ 7.16-7.32 (m, 4H), 5.13 (s, 1H), 4.65 (t, J=6.0 Hz, 1H), 2.56-2.64 (m, 2H), 1.44-1.63 (m, 12H), 0.90 (t, J=7.6 Hz, 6H).

Workup

customPurification by flash chromatography (10% 7M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-efb396136cff458baa20f7c85493184a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716529B2

Reaction notes

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