Methyl iodide → HCID 66762792, compound

HRID 573795Notes

Reaction equation

HRID 573795 reaction equation
[CH3:1][C:2]1([CH3:41])[CH2:11][C:10]2[N:9]=[C:8]([CH:12]([OH:14])[CH3:13])[C:7]3[C@@H:15]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[O:16][C:17]4([CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:6]=3[C:5]=2[C@@H:4]([O:33][C:34]([CH3:40])([C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:35])[CH2:3]1.[CH3:42]I>O1CCCC1>[CH3:42][O:14][CH:12]([C:8]1[C:7]2[C@@H:15]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)[O:16][C:17]3([CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:6]=2[C:5]2[C@@H:4]([O:33][C:34]([CH3:40])([C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:35])[CH2:3][C:2]([CH3:1])([CH3:41])[CH2:11][C:10]=2[N:9]=1)[CH3:13]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66762158HCID 66762158, compound

Product 1

HCID 66762792HCID 66762792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

70 mg 1-((3R,9S)-7,7-Dimethyl-3-(4-(trifluoromethyl)phenyl)-9-(2,3,3-trimethylbutan-2-yloxy)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-4-yl)ethanol are dissolved in 1.5 ml tetrahydrofurane. 27 mg Potassium-tert.-butylate are added, the mixture is stirred for 5 minutes and the 11 μl methyliodide are added. The mixture is stirred for 20 minutes and then partitioned between 0.1 M hydrochloric acid and dichloromethane. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried with sodium sulphate. The solvents are evaporated in vacuo and the residue is purified by preparative HPLC (Gemini C18, water/methanol/ammonia 90:10:0.1 to 0:100:0.1).

Workup

  1. stirringThe mixture is stirred for 20 minutes
  2. custompartitioned between 0.1 M hydrochloric acid and dichloromethane
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. dry with materialthe combined organic phases are dried with sodium sulphate
  5. customThe solvents are evaporated in vacuo
  6. customthe residue is purified by preparative HPLC (Gemini C18, water/methanol/ammonia 90:10:0.1 to 0:100:0.1)

Sources & evidence

ORD record
ord-5d82fd65bc09454ea29f1d0ab3a4c393
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

Loading…