Water → HCID 19106751, compound

HRID 1197444Notes

Reaction equation

HRID 1197444 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:37]=[CH:36][C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][C:21]3[CH:22]=[C:23]([C:28]4([O:34][CH3:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:24]=[C:25]([F:27])[CH:26]=3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)#[N:8].O.[OH-].[Na+]>C1COCC1>[NH2:8][CH2:7][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([S:20][C:21]3[CH:22]=[C:23]([C:28]4([O:34][CH3:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:24]=[C:25]([F:27])[CH:26]=3)=[CH:18][CH:19]=2)=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 19106754HCID 19106754, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19106751HCID 19106751, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1M in THF. 1.5 ml) was added dropwise to a stirred solution of 4-[3-(4-(4-cyanobenzyl)phenylthio)-5-fluorophenyl]-4-methoxytetrahydropyran (0.675 g) in THF (9 ml) and the mixture was stirred at ambient temperature for 1 hour. Water (5 ml) and 4N aqueous sodium hydroxide solution (5 ml) were added in turn. The mixture was extracted with diethyl ether. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was dissolved in diethyl ether (5 ml) and a solution of oxalic acid in diethyl ether was added. The precipitate was isolated. There was thus obtained the mono-oxalate salt of 4-[3-(4-(4-aminomethylbenzyl)phenylthio)-5-fluorophenyl]-4-methoxytetrahydropyran (0.34 g), m.p. 142°-146° C.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in diethyl ether (5 ml)
  6. additiona solution of oxalic acid in diethyl ether was added
  7. customThe precipitate was isolated

Sources & evidence

ORD record
ord-997cb3ea5778477698cb757efd5c80d9
Source dataset
uspto-grants-1994_01
Patent number
US05276037

Reaction notes

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