Methyl iodide → HCID 86586682, compound

HRID 2088150Notes

Reaction equation

HRID 2088150 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([OH:16])[CH2:15][C@@:9]1([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:10]([O:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39]I.[H-].[Na+]>C1COCC1>[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([O:16][CH3:39])[CH2:15][C@@:9]1([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:10]([O:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:27])([F:28])[F:26])[CH:22]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:20]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86586680HCID 86586680, compound

Product 1

HCID 86586682HCID 86586682, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-ol (Example 43; 22 mg 0.041 mmol), methyl iodide (0.5 ml), sodium hydride (40 mg, 1 mmol) and THF (2 ml) was stirred at room temperature for 24 hours, quenched quenched with saturated aqueous NH4Cl and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by preparative TLC on silica gel (iso-hexane:diethyl ether 30%) to give the title compound (17 mg, 75%).

Workup

  1. customquenched
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted into dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC on silica gel (iso-hexane:diethyl ether 30%)

Sources & evidence

ORD record
ord-77a9eae2993f49c28b383e1cd22ca29c
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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