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

HRID 723533Notes

Reaction equation

HRID 723533 reaction equation
[C@@H:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(Cl)(Cl)Cl.C[Si]([Br:18])(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>CS(C)=O>[Br:18][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

6

Reactant 4

HCID 6212ChloroformHCID 76113BromotrimethylsilaneHCID 736697(R)-Cyclohex-3-enecarboxylic acidHCID 178524570HCID 178524570, compound

Product 1

HCID 13076925(1R,4S,5R)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(R)-Cyclohex-3-enecarboxylic acid (2.30 g, 18.2 mmol) ([α]D=+83.8° (c=1, CHCl3)=88.2% e.e., resolved by the method of Schwartz et al, J. Am. Chem. Soc., 100, 5199, (1978)) was reacted with trimethylsilyl bromide and DMSO (by the method of Iwata et al, Heterocycles., 31, 987 (1990)) to give a white solid, (2.13 g, 10.4 mmol, 57%);

Workup

  1. custom, 31, 987 (1990)) to give a white solid, (2.13 g, 10.4 mmol, 57%)

Sources & evidence

ORD record
ord-f0fff56d60d24bb794ea67f2832e4639
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

Loading…