Water → HCID 11589988, compound

HRID 1790722Notes

Reaction equation

HRID 1790722 reaction equation
O1[CH2:6][CH2:5][CH2:4][O:3][O:2]1.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C(O[BH-](O[C:30](=[O:32])[CH3:31])OC(=O)C)(=O)C.[Na+].O>ClCCl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][C:8]([NH:7][CH:18]2[CH2:6][CH2:5][C:4]3([O:3][O:2][CH:31]([C:14]([C:11]4[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=4)=[CH2:15])[CH2:30][O:32]3)[CH2:16][CH2:17]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71024-AminobiphenylHCID 5049666Sodium triacetoxyborohydrideHCID 19593658CID 19593658

Product 1

HCID 11589988HCID 11589988, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of trioxane 3a (0.40 g, 1.45 mmol) and 4-aminobiphenyl (0.30 g, 1.82 mmol) in dichloromethane (20 ml) acetic acid (1 ml) was added and reaction mixture was stirred at room temp for half an hour. Sodium triacetoxyborohydride (0.46 g, 3.63 mmol) was added slowly and it was stirred for 3 h at room temperature. Reaction mixture was then poured into water and extracted with CH2Cl2 (2×20 ml). Combined organic layer was dried over anhyd. Na2SO4, concentrated under vacuum and crude product was chromatographed over silica gel using benzene-hexane (50:50) as eluant to furnish amino functionalized 1,2,4-trioxane 4ad as an inseparable mixture of diastereomers (0.44 g, 70.5% yield), m.p. 118–120° C.

Workup

  1. additionwas added
  2. customreaction mixture
  3. stirringit was stirred for 3 h at room temperature
  4. customReaction mixture
  5. extractionextracted with CH2Cl2 (2×20 ml)
  6. customCombined organic layer was dried over anhyd
  7. concentrationNa2SO4, concentrated under vacuum and crude product
  8. customwas chromatographed over silica gel
  9. customto furnish amino functionalized 1,2,4-trioxane 4ad
  10. additionas an inseparable mixture of diastereomers (0.44 g, 70.5% yield), m.p. 118–120° C.

Sources & evidence

ORD record
ord-8e433fe3a5b94f9cb05d2594a2d623bf
Source dataset
uspto-grants-2006_07
Patent number
US07071226B1

Reaction notes

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