Toluene → 2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane

HRID 2088172Notes

Reaction equation

HRID 2088172 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[F:18][C:19]([F:57])([F:56])[C:20]1[CH:21]=[C:22]([CH2:30][O:31][C@@H:32]2[CH2:38][CH2:37][C@@H:36]3[N:39]([CH2:40][CH:41]=[CH2:42])[C@@:33]2([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:34][C@H:35]3[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>C1COCC1>[F:56][C:19]([F:18])([F:57])[C:20]1[CH:21]=[C:22]([CH2:30][O:31][CH:32]2[CH2:38][CH2:37][CH:36]3[N:39]([CH2:40][CH:41]=[CH2:42])[C:33]2([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:34][CH:35]3[C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86586707(1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 865867082-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium bis(trimethylsilyl)amide in toluene (0.5M, 1.5 ml, 0.75 mmol) was added to a stirred solution of (1R*,2R*,5S*,6R*)-2-{[3,5-bis(trifluoromethyl)-phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane (Example 80; 362 mg, 0.635 mmol) in THF (5 ml) at +5° C. The mixture was stirred for 15 minutes and quenched with saturated aqueous NH4Cl and extracted into diethyl ether. The organic extracts was washed with water, dried (Na2SO4) and concentrated to give the title compound as a 4.6:1 mixture diastereoisomers.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted into diethyl ether
  3. washThe organic extracts was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb2bdc74420345af8d54a91384345c2b
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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