Dimethyl Sulfoxide → (1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

HRID 723536Notes

Reaction equation

HRID 723536 reaction equation
[C@H:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C[Si]([Br:14])(C)C.CS(C)=O.C(N(CC)C(C)C)(C)C.C1C=C(NS(C2C=CC(N/N=C3/C=CC(C(C(O)=O)=C/3)=O)=CC=2)(=O)=O)N=CC=1>C(Cl)(Cl)Cl>[Br:14][C@H:4]1[C@@H:5]2[CH2:6][C@@H:1]([C:7](=[O:9])[O:8]2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 76113BromotrimethylsilaneHCID 81531DiisopropylethylamineHCID 7128364(S)-(-)-3-Cyclohexene-1-carboxylic AcidHCID 178524570HCID 178524570, compound

Product 1

HCID 10878278(1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(S)-Cyclohex-3-enecarboxylic acid (1.98 g, 15.7 mmol) ([α]D=−92.7° (c=1, CHCl3)=97.5% e.e., resolved by the method of Schwartz et al, J. Am. Chem. Soc., 100, 5199, (1978)) was reacted with trimethylsilyl bromide (4.10 mL, 31.3 mmol), DMSO (2.23 mL, 31.3 mmol), and N,N-diisopropylethylamine (4.45 mL, 31.3 mmol) (by a modification of the method of Iwata et al, Heterocycles., 31, 987 (1990)) to give a white solid, (2.91 g, 14.2 mmol, 90%);

Workup

  1. custom, 31, 987 (1990)) to give a white solid, (2.91 g, 14.2 mmol, 90%)

Sources & evidence

ORD record
ord-4ad45c396ab74283bc98d5d2bb1b5c95
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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