Water → Cis-1-[4-(benzoxazol-2-yl)benzyloxy]-2-triphenylmethylaminocyclohexane

HRID 2399735Notes

Reaction equation

HRID 2399735 reaction equation
[C:1]1([C:7]([NH:20][C@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[OH:27])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1.O>C1COCC1>[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[C:39]1[CH:46]=[CH:45][C:42]([CH2:43][O:27][C@@H:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C@@H:21]2[NH:20][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 54233547cis-2-Triphenylmethylaminocyclohexanol

Product 1

HCID 54326495Cis-1-[4-(benzoxazol-2-yl)benzyloxy]-2-triphenylmethylaminocyclohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cis-2-triphenylmethylaminocyclohexanol (1.52 g; 4.25 mmol) is added to a solution of sodium hydride (256 mg; 60%; 6.4 mmol) in 20 ml dry THF and refluxed overnight. The solution is cooled, 4-(benzoxazol-2-yl)benzyl bromide (1.3 g; 4.5 mmol) is added in one portion and refluxed for 5 hrs. This is then poured into water and extracted with 2×100 ml CH2Cl2, dried (Na2SO4), concentrated to dryness and flash chromatographed using 4:1 8:1; hexane:EtOAc to obtain Cis-1-[4-(benzoxazol-2-yl)benzyloxy]-2-triphenylmethylaminocyclohexane which is used directly in the next step.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe solution is cooled
  3. temperaturerefluxed for 5 hrs
  4. extractionextracted with 2×100 ml CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness and flash
  7. customchromatographed

Sources & evidence

ORD record
ord-8b9e1e4766494f58a044e319349d77fa
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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