Iodine → HCID 66762583, compound

HRID 573769Notes

Reaction equation

HRID 573769 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([C@@H:24]([C:26]3[S:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)[OH:25])=[C:11]([C:35]3[CH2:39][CH2:38][CH2:37][CH:36]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I:40]I.C(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.C(OCC)C>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:26]4[S:27][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:29][CH:30]=4)[O:25][C:35]4([CH2:39][CH2:38][CH2:37][CH:36]4[I:40])[C:11]=3[C:10]1=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 807Iodine2×HCID 516892Sodium BicarbonateHCID 66762448HCID 66762448, compound

Product 1

HCID 66762583HCID 66762583, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 67 mg (S)—((S)-5-(tert-butyldimethylsilyloxy)-4-cyclopentenyl-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(5-(trifluoromethyl)thiophen-2-yl)methanol in 1 ml tetrahydrofurane and 1 ml acetonitrile are added under nitrogen 29 mg sodium bicarbonate and a solution of 88 mg of iodine in 200 μl tetrahydrofurane and the reaction is monitored by thin layer chromatography. In the case of low conversion the same amounts of sodium bicarbonate and iodine solution are added up to two times. The mixture is then diluted with diethylether and washed with saturated aqueous sodium sulfite solution and brine. After drying with sodium sulphate the solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 98:2 to 80:20).

Workup

  1. washwashed with saturated aqueous sodium sulfite solution and brine
  2. dry with materialAfter drying with sodium sulphate the solvents
  3. customare evaporated in vacuo
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 98:2 to 80:20)

Sources & evidence

ORD record
ord-63f3c878926146d7aca9c74fa33e5a1b
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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