Water → 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

HRID 1531394Notes

Reaction equation

HRID 1531394 reaction equation
[CH3:1][CH2:2][CH2:3]CCCC.C(C1C=[C:17](C(C)(C)C)[CH:16]=[C:14]([OH:15])[C:13]=1[OH:23])(C)(C)C.[OH2:24]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:1][C:2]1([CH3:3])[O:23][CH2:13][CH:14]2[CH:16]([O:15]2)[CH2:17][O:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 8900HeptaneHCID 660993,5-Di-tert-butylcatechol

Product 1

HCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Heptane (2 ml) was added to 3,5-di-t-butylcatechol (617 mg), and titanium tetraisopropoxide (Ti(OPri)4, 818 μl) was added under a nitrogen atmosphere. The mixture was stirred for 20 min at room temperature. (R)-1-phenethylamine (1.79 ml), water (20 μl) and 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane (compound [1′], 2.0 g) obtained by a known method were successively added with stirring, and the mixture was stirred at room temperature for 20 hr. Heptane (4.6 ml) was added to the reaction mixture and the mixture was stirred under ice-cooling for 1 hr. The resulting crystals were collected by filtration to give (5R,6S)-2,2-dimethyl-6-[(R)-1-phenethylamino]-1,3-dioxepan-5-ol (compound [3′], 2.14 g, yield 57%).

Workup

  1. additionwas added under a nitrogen atmosphere

Sources & evidence

ORD record
ord-b867863ea3ab42238834384863809c85
Source dataset
uspto-grants-2001_03
Patent number
US06197966B1

Reaction notes

Loading…