Potassium sodium tartarate → (1R,2S,5S) 6,6-dimethyl-3-oxa-bicyclo(3,1,0)hexane-2-ol

HRID 2232609Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:19])[C@H:17]2[C@@H:13]1[CH2:14][O:15][C:16]2=[O:18].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1>[CH3:11][C:12]1([CH3:19])[C@H:17]2[C@@H:13]1[CH2:14][O:15][C@@H:16]2[OH:18]

Participants

Conditions

Temperature: -65 °C

Procedure

404 ml of a toluene solution of 1.2 moles of diisobutyl aluminum hydride were slowly added at -70° C. to a solution of 60 g of the product of Step A in 720 ml of toluene and the mixture was stirred at -65° C. for 16 minutes and slowly poured into an aqueous solution of sodium potassium tartrate. The mixture was stirred and allowed to stand and the decanted aqueous phase was extracted with ether. The combined organic phases were evaporated to dryness and the residue was taken up in methylene chloride. The solution was evaporated to dryness under reduced pressure to obtain 56.7 g of (1R,2S,5S) 6,6-dimethyl-3-oxa-bicyclo (3,1,0) hexane-2-ol with a boiling point of ≃50° C. at 0.5 mm Hg and a specific rotation of [α]D20 =+66.5° (c=1% in ethanol).

Workup

stirringThe mixture was stirred
extractionthe decanted aqueous phase was extracted with ether
customThe combined organic phases were evaporated to dryness
customThe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-99585541a00e45a1a3194309d7a2d9dc
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788305

Reaction notes

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