Diisopropylamine → Bicyclo(3.1.0)hexan-2-one, 5-(1-methylethyl)-

HRID 971964Notes

Reaction equation

C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C(N[CH:13]([CH3:15])[CH3:14])(C)C.[CH2:16]([Li])[CH2:17][CH2:18]C.[I-].C[S+](C)(C)=[O:24]>C1COCC1>[CH3:16][CH:17]([C:6]12[CH2:7][CH:5]1[C:14](=[O:24])[CH2:13][CH2:15]2)[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a THF solution of lithium diisopropylamide prepared from 26 mM of diisopropylamine and 26 mM of n-butyllithium, 6.16 g (28 mM) of trimethylsulfoxonium iodide were added under ice cooling, and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. This reaction mixture was poured dropwise into a solution of 2.48 g (20 mM) of CP in 20 ml of THF during 4 hours. After the reaction was carried out at room temperature for 3 hours, the treatments were carried out as described in Example 8. 2.48 g (89% yield) of crude product were produced, from which 1.76 g (63% yield) of sabina ketone were obtained by distillation.

Workup

additionwere added under ice cooling
waitat room temperature for 2 hours
waitAfter the reaction was carried out at room temperature for 3 hours

Sources & evidence

ORD record: ord-856e7ccf7cf44477a0f6cb6105f5557f
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04162258

Reaction notes

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