Methanol → HCID 9799463, compound

HRID 1018483Notes

Reaction equation

HRID 1018483 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[O:4][NH:3]1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH:22]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl>[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[O:4][N:3]1[CH2:22][C:21]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 8419VeratraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18401526HCID 18401526, compound

Product 1

HCID 9799463HCID 9799463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 0.5 ml of a 0.05M solution of 3,5-dimethyl-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine in dichloromethane. 0.5 ml of a 0.75M solution of 3,4-dimethoxybenzaldehyde in dichloromethane, and 0.5 ml of a 0.75M solution of sodium triacetoxyborohydride in dichloromethane was stirred at ambient temperature for 19 h. Methanol (1.0 ml) was added with stirring and the mixture applied to a methanol washed 500 mg Isolute SCX cartridge (Jones Chromatography). The absorbent was washed with methanol (2.5 ml) and then eluted with 2M ammonia in methanol (2.5 ml). The eluate was concentrated to dryness using a centrifugal evaporator and the residue dissolved in chloroform (2 ml) and added to methylisocyanate-polystyrene (loading 1.0 meq/g, 100 mg). This suspension was shaken gently for 19 h, then filtered and resin washed with chloroform (2×2 ml). Removal of the solvent from the combined filtrates by centrifugal evaporation gave 3,5-dimethyl-2-(3,4-dimethoxybenzyl)-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine. 1H NMR (CDCl3) δ 1.23(3H, d), 1.49(3H, s), 3.39(1H, m), 3.62(1H, d), 3.70(3H, s), 3.79(3H, s), 3.83(3H, s), 4.05(1H, d), 4.92(1H, s), 5.61 (1H, d), 6.64 (3 H, m),6.81 (2H, d), 7.22 (2H, d).

Workup

  1. washwashed 500 mg Isolute SCX cartridge (Jones Chromatography)
  2. washThe absorbent was washed with methanol (2.5 ml)
  3. washeluted with 2M ammonia in methanol (2.5 ml)
  4. concentrationThe eluate was concentrated to dryness
  5. customa centrifugal evaporator
  6. dissolutionthe residue dissolved in chloroform (2 ml)
  7. additionadded to methylisocyanate-polystyrene (loading 1.0 meq/g, 100 mg)
  8. stirringThis suspension was shaken gently for 19 h
  9. filtrationfiltered
  10. washresin washed with chloroform (2×2 ml)
  11. customRemoval of the solvent from the combined filtrates
  12. customby centrifugal evaporation

Sources & evidence

ORD record
ord-fa4c672c714f42399814aeeba4ef981e
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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