Sodium hydride → HCID 178420365, compound

HRID 2399746Notes

Reaction equation

HRID 2399746 reaction equation
[C:1]1([C:7]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]2)([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>C1COCC1>[C:1]1([C:7]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([O:27][CH2:43][C:42]3[CH:45]=[CH:46][C:39]([C:31]4[O:30][C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=5[N:32]=4)=[CH:40][CH:41]=3)[CH2:23][CH2:22]2)([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)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 178521610HCID 178521610, compound

Product 1

HCID 178420365HCID 178420365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of trans-4-triphenylmethylaminocyclohexanol (3.18 g; 8.90 mmol) is 100 ml THF is added sodium hydride (60%; 0.320 g; 13.35 mmol) and this is followed by the addition of 4-(benzoxazol-2-yl)benzyl bromide after about 1 hr. The mixture is heated at reflux for 1 week, cooled, concentrated in vacuo and dissolved in about 40 ml CH2Cl2 ; hexane:ethylacetate (9:1 ). The solid material is filtered off and the residue flash chromatographed using hexane:ethylacetate; 7:1 to obtain trans-4-triphenylmethylamino-[4-(benzoxazol-2-yl)benzyloxy]cyclohexane as a white solid which is used directly in the next step.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 week
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in about 40 ml CH2Cl2
  6. filtrationThe solid material is filtered off
  7. customthe residue flash chromatographed

Sources & evidence

ORD record
ord-7ed20466722e4d569f17c1d5eabf7716
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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