Water → HCID 54316056, compound

HRID 1005147Notes

Reaction equation

HRID 1005147 reaction equation
[C:1]([NH:9][NH:10][C:11](=[O:45])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]2[O:33][CH2:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=2)=[CH:16][CH:15]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>C[Si](C)(C)N[Si](C)(C)C.O1CCCC1>[CH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:43]=[CH:44][C:35]=1[CH2:34][O:33][CH:21]1[CH:20]([C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][C:11]3[O:45][C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[N:9][N:10]=3)=[CH:19][CH:18]=2)[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 86604473HCID 86604473, compound

Product 1

HCID 54316056HCID 54316056, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

A solution of 106 mg (0.174 mmol) of tert-butyl (3RS,4RS)-4-[4-[3-(N'-benzoyl-hydrazino)-3-oxo-propyl]-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate in 1.5 ml of hexamethyidisilazane was treated with 39 μl (0.039 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and heated to reflux for 20 hours. For the working-up, the reaction mixture was treated with 50 ml of a 1:1 mixture of methylene chloride and water, the organic phase was subsequently separated and the aqueous phase was back-extracted twice with 25 ml of methylene chloride each time. The combined organic phases were dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel with a 7:3 mixture of hexane and ethyl acetate as the eluent. There were obtained 70 mg (68% of theory) of tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-[4-[2-(5-phenyl-[1,3,4]oxadiazol-2-yl)-ethyl]-phenyl]-piperidine-1-carboxylate as a colourless solid; MS: 590 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. customthe organic phase was subsequently separated
  4. extractionthe aqueous phase was back-extracted twice with 25 ml of methylene chloride each time
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel with a 7:3 mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1258901697c944ae9221fc7808bef6c8
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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