2-Bromomethylnaphthalene → HCID 18461542, compound

HRID 2303454Notes

Reaction equation

HRID 2303454 reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH2:7][CH:8]=[CH:9][CH:2]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1>C1COCC1>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][CH:4]1[C:5](=[O:6])[O:1][CH:2]2[CH:9]=[CH:8][CH2:7][CH:3]12

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 556356HCID 556356, compoundHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 18461542HCID 18461542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to the procedure of Example 1, the title compound was prepared from 0.31 g (2.5 mmol) of 3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one, 2.5 ml of a 1 molar lithium bis-(trimethylsilyl)-amide solution in THF and 0.55 g (2.5 mmol) of 2-(bromomethyl)-naphthalene in 10 ml of THF. Yield: 498 mg (75.4%) of a pale yellow oil (Example 21). Diastereomer mixture: 94:6 (HPLC) MS (EI): m/e=264 [M+] The separation into the diastereomers and enantiomers is carried out using preparative HPLC: Example 22, 23, 24 and 25.

Workup

  1. customDiastereomer mixture: 94:6 (HPLC) MS (EI): m/e=264 [M+] The separation into the diastereomers and enantiomers

Sources & evidence

ORD record
ord-1da4ad93c1644315b4d3540854454bcf
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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