Acetone → HCID 54354149, compound

HRID 543559Notes

Reaction equation

HRID 543559 reaction equation
C(C1NC(=O)C1)C=C.C([Li])CCC.CC(C)=O.[CH2:18]([C@@H:21]1[NH:24][C:23](=[O:25])[C@H:22]1[C:26]([OH:29])([CH3:28])[CH3:27])[CH:19]=[CH2:20]>O1CCCC1.CCCCCC.C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH2:18]([CH:21]1[NH:24][C:23](=[O:25])[CH:22]1[C:26]([OH:29])([CH3:28])[CH3:27])[CH:19]=[CH2:20]

Participants

10

Reactant 4

HCID 180AcetoneHCID 15515568485-52-9HCID 70504241HCID 70504241, compoundHCID 178418339Butyllithium

Product 1

HCID 54354149HCID 54354149, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-allylazetidin-2-one (0.25 g) in dry tetrahydrofuran (25 ml) was stirred at -5° C. under argon and treated with a 2.5 M solution of n-butyl-lithium in hexane (3.0 ml). A period of 1 hour was allowed for the dianion to form and dry acetone (1.0 ml) was then added. After a further 10 mins. water (5 ml) was added to the reaction mixture, which was then concentrated to about 10 ml in volume. This was extracted with methylene chloride (20 ml), and the organic phase was then dried over sodium sulphate and concentrated. The residue was chromatographed on silica gel 60 (<230 mesh) eluting with ethyl acetate/60°-80° petroleum ether 1:1 grading to ethyl acetate to give the cis and trans aldol products. The least polar isomer was cis-4-allyl-3-(2-hydroxy-2-propylazetidin)2-one (0.029 g); m.p. 144° (ethyl acetate/60°-80° petroleum ether). ν max (CHCl3) 3400, 2980, 2930, 1745 and 1640 cm-1 ; δ(CDCl3) 1.35 (3H, s), 1.51 (3H, s), 2.18 (1H, br), 2.5-2.9 (2H, m), 3.28 (1H, d, J 5 Hz), 3.85 (1H, td J 9 and 5 Hz), 4.9-6.1 (3H, m), and 7.20 (1H, br) (Found: C, 64.2; H, 9.0; N, 8.2%. C9H15NO2 requires C, 63.9; H, 8.9 and N, 8.3%). The more polar isomer was trans-4-allyl-3-(2-hydroxy-2-propyl)azetidin-2-one (0.042 g); νmax (CHCl3) 3400, 2980, 2930, 1750 and 1640 cm-1, δ(CDCl3) 1.29 (3H, s), 1.39 (3H, s), 2.41 (3H, br t J 6 Hz), 2.88 (1H, d, J 2 Hz), 3.69 (1, 6d J 6 and 2 Hz), 4.9-5.4 (2H, m), 5.89 (1H, ddt J 18, 9 and 6 Hz), and 6.50 (1H, br).

Workup

  1. customA period of 1 hour
  2. customto form
  3. concentrationwas then concentrated to about 10 ml in volume
  4. extractionThis was extracted with methylene chloride (20 ml)
  5. dry with materialthe organic phase was then dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel 60 (<230 mesh)
  8. washeluting with ethyl acetate/60°-80° petroleum ether 1:1 grading to ethyl acetate
  9. customto give the cis and trans aldol products

Sources & evidence

ORD record
ord-c1f99cf38cfb44e1898c53fff040aab1
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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