1-Ethynyl-1-cycloheptanol → HCID 86628453, compound

HRID 2098482Notes

Reaction equation

HRID 2098482 reaction equation
[C:1]([C:3]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].Br[C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH:15]=[CH:16][CH:17]=1>>[F:24][C:23]([F:25])([F:26])[C:22]([NH:21][CH2:20][CH2:19][CH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:2]#[C:1][C:3]2([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:13]=1)=[O:27]

Participants

3

Reactant 2

HCID 1377281-Ethynyl-1-cycloheptanolHCID 57608389N-(3-(3-bromophenyl)propyl)-2,2,2-trifluoroacetamide

Product 1

HCID 86628453HCID 86628453, compound

Procedure

Coupling of 1-ethynylcycloheptanol with bromide 10 following the method used to prepare Example 7. Purification by flash chromatography (20% EtOAc-hexanes) gave 2,2,2-trifluoro-N-(3-(3-((1-hydroxycycloheptyl)ethynyl)phenyl)propyl)acetamide as a pale yellow oil. Yield (1.78 g, 60%): 1H NMR (400 MHz, DMSO-d6) δ9.40 (s, 1H), 7.26 (t, J=7.6 Hz, 1H), 7.17-7.22 (m, 3H), 5.26 (s, 1H), 3.16 (q, J=6.0 Hz, 2H), 2.56 (t, J=7.2 Hz, 2H), 1.91-1.97 (m, 2H), 1.73-1.79 (m, 4H), 1.45-1.63 (m, 8H).

Workup

  1. customto prepare Example 7
  2. customPurification by flash chromatography (20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-7af53f718acb4dadb743dac251f51dad
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

Loading…