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

HRID 1437333Notes

Reaction equation

HRID 1437333 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.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>CS(C)=O>[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

6

Reactant 4

HCID 76113BromotrimethylsilaneHCID 81531DiisopropylethylamineHCID 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, 98.2% e.e, (2.30 g, 18.2 mmol) [Schwartz et al, J. Am. Chem. Soc., 100, 5199, (1978)] was reacted with trimethylsilyl bromide (3.01 mL, 22.8 mmol), DMSO (1.62 mL) and N,N-diisopropylethylamine (3.97 mL, 22.8 mmol) [by the method of Iwata et al, Heterocycles., 31, 987 (1990)] to give a white solid, (2.13 g, 57%).

Workup

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

Sources & evidence

ORD record
ord-ec1be874917e4620bb8cb74a52ef9c77
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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