Trimethylaluminum → HCID 18646603, compound

HRID 1030658Notes

Reaction equation

HRID 1030658 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].[CH3:20][Al](C)C>CCCCCC>[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]([CH3:20])[C@@H:10]1[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 18646605HCID 18646605, compound

Product 1

HCID 18646603HCID 18646603, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Under argon to a solution of (±)-(1S,2R,3R)-3-tert-butoxycarbonylamino -1,2-epoxy-1,2,3,4-tetrahydro-naphthalene (108 mg) in hexane (10 ml) was added a 2 M solution of trimethylaluminum in hexane (0.30 ml), the mixture was heated under reflux for 31/2 hours and was quenched by addition of a 2 M aqueous solution of ammonium chloride adjusted to pH 8 with ammonium hydroxide. The resulting suspension was extracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate and evaporated under vacuum to give a colorless oil which was purified by preparative thin layer chromatography on silica gel (elution with ethyl acetate:cyclohexane, 3:8) to afford the title compound as a solid (32 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 31/2 hours
  3. customwas quenched by addition of a 2 M aqueous solution of ammonium chloride
  4. extractionThe resulting suspension was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customto give a colorless oil which
  8. customwas purified by preparative thin layer chromatography on silica gel (elution with ethyl acetate:cyclohexane, 3:8)

Sources & evidence

ORD record
ord-9d3f9fed11684780b72a9eaaf7e04619
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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