Sodium Iodide → 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidine

HRID 1722267Notes

Reaction equation

HRID 1722267 reaction equation
[C:1]([NH:8][C@H:9]([CH:17]1[CH2:19][O:18]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Na+].[I-:21].C[Si](Cl)(C)C.[F-].[CH2:28]([N+](CCCC)(CCCC)CCCC)[CH2:29][CH2:30]C.C([O-])(O)=O.[Na+]>C(#N)C.C1COCC1.C(COC)OC>[C:1]([N:8]1[C@@H:9]([CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:17]([CH2:19][I:21])[O:18][C:29]1([CH3:30])[CH3:28])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 13892786Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine

Product 1

HCID 1317160313-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidine

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.4 g of Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine, 1.3 g of NaI and 1.1 ml of trimethylsilyl chloride are dissolved in 100 ml of acetonitrile, and the solution is stirred at R.T. for 1.5 h. Then 8.7 ml of a 1M solution of tetrabutylammonium fluoride in THF and 5.3 ml of dimethoxyethane are injected in. The mixture is stirred at R.T. for 2.5 h and then 200 ml of saturated aqueous NaHCO3 solution are added, and the mixture is extracted 3 times with 200 l of MTB. Drying over Na2SO4 and concentration in vacuo is followed by chromatography on silica gel (mobile phase MTB/diisopropyl ether 1:2) resulting in the title compound as a colorless oil.

Workup

  1. stirringThe mixture is stirred at R.T. for 2.5 h
  2. extractionthe mixture is extracted 3 times with 200 l of MTB
  3. dry with materialDrying over Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-767a9097136e48b9acde236e508bb6fa
Source dataset
uspto-grants-1989_08
Patent number
US04855286

Reaction notes

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