HCID 18646605, compound → HCID 19995520, compound

HRID 1030656Notes

Reaction equation

HRID 1030656 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]2[O:19][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Ti]>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([O:5][CH:1]([CH3:3])[CH3:2])[CH:10]1[OH:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 18646605HCID 18646605, compound

Product 1

HCID 19995520HCID 19995520, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 887MethanolSolvent

Conditions

Temperature
96 °C

Procedure

Under argon to a solution of (±)-(1S,2R,3R)-3-tertbutoxycarbonylamino -1,2-epoxy-1,2,3,4-tetrahydro- naphthalene (96 mg) in methanol (4 ml) was added titanium isopropoxyde (0.19 ml). The mixture was warmed for 14 hours in an oil bath maintained at 96° C. Evaporation of the warm mixture under an argon flow gave a residue which was purified on a silica gel column (22 g, elution with ethyl acetate:cyclohexane, 1:4). After evaporation of solvents was recovered an oil which was crystallized from a pentane/diethyl ether mixture to afford the title compound as a white solid (56 mg).

Workup

  1. temperatureThe mixture was warmed for 14 hours in an oil bath
  2. customEvaporation of the warm mixture under an argon flow
  3. customgave a residue which
  4. customwas purified on a silica gel column (22 g, elution with ethyl acetate:cyclohexane, 1:4)
  5. customAfter evaporation of solvents
  6. customwas recovered an oil which
  7. customwas crystallized from a pentane/diethyl ether mixture

Sources & evidence

ORD record
ord-9de35b5c631b4412b75268faf4fd55ac
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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