Potassium Iodide → HCID 22856087, compound

HRID 2399739Notes

Reaction equation

HRID 2399739 reaction equation
[C:1]1([C:7]([NH:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][C@H:22]2[OH:26])([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.[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1.[I-].[K+]>C1COCC1.CN(C=O)C>[C:1]1([C:7]([NH:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][C@H:22]2[O:26][CH2:40][C:39]2[CH:42]=[CH:43][C:36]([C:28]3[O:27][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[N:29]=3)=[CH:37][CH:38]=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

6

Reactant 3

HCID 4875Potassium IodideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 54023768HCID 54023768, compound

Product 1

HCID 22856087HCID 22856087, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of trans-2-triphenylmethylaminocyclopentanol (4.76 g; 13.85 mmol), is added Nail (60%; 0.83 g; 20.78 mmol) in 100 ml THF and 20 ml DMF. This mixture is stirred for 1 hr. and then 4-(benzoxazol-2-yl)benzyl bromide (3.99 g; 13.85 mmol) is added followed by potassium iodide (pinch). The reaction mixture is stirred for 72 hrs., quenched with water, concentrated in vacuo and flash chromatographed using 9:1; hexane:EtOAc to obtain trans-2-triphenylmethylamino-[4-(benzoxazol-2-yl)benzyloxy]cyclopentane which is used directly in the next step.

Workup

  1. stirringThe reaction mixture is stirred for 72 hrs
  2. custom, quenched with water
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Sources & evidence

ORD record
ord-100f600a60df46d8b59012e4321923a9
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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