Water → HCID 11532007, compound

HRID 1790721Notes

Reaction equation

HRID 1790721 reaction equation
O1[CH2:6][CH2:5][CH2:4][O:3][O:2]1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](O[C:30](=[O:32])[CH3:31])OC(=O)C)(=O)C.[Na+].O>ClCCl>[C:9]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][CH:18]1[CH2:6][CH2:5][C:4]2([O:3][O:2][CH:31]([C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=3)=[CH2:15])[CH2:30][O:32]2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 70152-AminobiphenylHCID 5049666Sodium triacetoxyborohydrideHCID 19593658CID 19593658

Product 1

HCID 11532007HCID 11532007, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To mixture of trioxane 3a (0.50 g, 1.82 mmol) and 2-aminobiphenyl (0.38 g, 2.27 mmol) in dichloromethane (20 ml) acetic acid was added (1 ml) and reaction mixture was stirred at room temp for half an hour. Sodium triacetoxyborohydride (0.58 g, 2.73 mmol) was added slowly and it was stirred for 3 h at room temperature. The 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 4ab as oil (upper Rf, 0.17 g, 21.8% yield) and 4ac (lower Rf, 0.25 g, 32.6% yield), m.p. 74–76° C.

Workup

  1. additionwas added
  2. custom(1 ml) and reaction mixture
  3. stirringit was stirred for 3 h at room temperature
  4. extractionextracted with CH2Cl2 (2×20 ml)
  5. customCombined organic layer was dried over anhyd
  6. concentrationNa2SO4, concentrated under vacuum and crude product
  7. customwas chromatographed over silica gel
  8. customto furnish amino functionalized 1,2,4-trioxane 4ab as oil (upper Rf, 0.17 g, 21.8% yield) and 4ac (lower Rf, 0.25 g, 32.6% yield), m.p. 74–76° C.

Sources & evidence

ORD record
ord-cc10fa94f3074812be93f370e5820499
Source dataset
uspto-grants-2006_07
Patent number
US07071226B1

Reaction notes

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