1,2-Dichloroethane → HCID 22350153, compound

HRID 896293Notes

Reaction equation

HRID 896293 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][NH2:22])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:48]CCCl>>[ClH:48].[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][NH:22][CH:26]4[CH2:27][CH2:28][O:23][CH2:24][CH2:25]4)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 102678372-[1-(Benzenesulfonyl)indol-4-yl]oxyethanamine

Product 1

HCID 22350153HCID 22350153, compound

Procedure

A mixture of 2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylamine (0.316 g, 1.0 mmol), tetrahydro-4H-pyran-4-one (0.09 ml, 1.00 mmol) and sodium triacetoxyborohydride (0.312 g, 1.4 mmol) in 1,2-dichloroethane is treated with acetic acid (0.06 ml) at room temperature, stirred under nitrogen for 18 hr, quenched with concentrated aqueous NH4OH and diluted with methylene chloride and water. The aqueous layer is separated and extracted with methylene chloride. The organic layer and extracts are combined, washed with saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05) to afford the free amine of the title product as a clear oil, 0.36 g (90%).

Workup

  1. customquenched with concentrated aqueous NH4OH
  2. additiondiluted with methylene chloride and water
  3. customThe aqueous layer is separated
  4. extractionextracted with methylene chloride
  5. washwashed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05)

Sources & evidence

ORD record
ord-65514b277a5d4d2cbd44014b230553bb
Source dataset
uspto-grants-2005_07
Patent number
US06919354B2

Reaction notes

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