Sodium sulfate decahydrate → (4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol

HRID 732175Notes

Reaction equation

HRID 732175 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[CH:30][CH:31]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 23111810Methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 23111783(4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanolYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to a solution of methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate (535 mg, 1.25 mmol) in tetrahydrofuran (20 mL) was added 1.5M diisobutyl aluminum hydride toluene solution (2.4 mL, 3.64 mmol). The mixture was stirred at room temperature for 2 hr and sodium sulfate 10 hydrate (1.29 g, 4 mmol) was added. The mixture was stirred at room temperature for 1 hr. The resulting insoluble materials were filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:3) to give the title compound (409 mg, yield 81%) as a colorless oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. filtrationThe resulting insoluble materials were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:3)

Sources & evidence

ORD record
ord-3beba905aec940398508a83e6246b3d3
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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