Methyl iodide → HCID 20461605, compound

HRID 543561Notes

Reaction equation

HRID 543561 reaction equation
[CH:1](NC1CCCCC1)(C)C.C([Li])CCC.[CH2:16]([CH:19]1[N:22]([Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:21](=[O:30])[CH2:20]1)[CH:17]=[CH2:18].IC>O1CCCC1.CCCCCC.C(O)(=O)C>[CH2:16]([CH:19]1[N:22]([Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[C:21](=[O:30])[CH:20]1[CH3:1])[CH:17]=[CH2:18]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 62386CyclohexylisopropylamineHCID 128821041-[tert-Butyl(dimethyl)silyl]-4-(prop-2-en-1-yl)azetidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 20461605HCID 20461605, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

N-Isopropylcyclohexylamine (12.4 g) in dry tetrahydrofuran (300 ml) was treated with 2 M n-butyllithium in n-hexane (44 ml) at -78° under argon. After five minutes 4-allyl-1-t-butyldimethylsilylazetidin-2-one (9.0 g) in dry tetrahydrofuran (100 ml) was added. Thirty minutes later iodomethane (70 ml) was added. The solution was stirred at -78° for 30 minutes and at room temperature for 2 hours, after which acetic acid (5.0 ml) was added. The solution was evaporated and partitioned between ethyl acetate and water. The organic phase was separated, dried (Na2SO4), evaporated and chromatographed on silica gel 60 (230 mesh) eluting with ethylacetate:petroleum ether (60-80) 1:3 to give as a mixture of two isomers 4-allyl-1-t-butyldimethylsilyl-3-methylazetidin-2-one (8.0 g).

Workup

  1. customThe solution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed on silica gel 60 (230 mesh)
  7. washeluting with ethylacetate

Sources & evidence

ORD record
ord-dcd071e9f6494e31b760d8e5ddaa2c2c
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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