Tetrahydrofuran → HCID 12800412, compound

HRID 543556Notes

Reaction equation

HRID 543556 reaction equation
[CH:1](NC1CCCCC1)([CH3:3])[CH3:2].C([Li])CCC.[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21](=[O:53])[CH2:20]1)[CH:17]=[CH2:18].[O:54]1CCCC1>CCCCCC>[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:21](=[O:53])[CH:20]1[C:1]([OH:54])([CH3:3])[CH3:2])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 62386CyclohexylisopropylamineHCID 127969694-Allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 12800412HCID 12800412, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of N-isopropylcyclohexylamine (0.60 g) in dry tetrahydrofuran (10 cm3) was stirred under argon and cooled to -78°. This was treated with a 2.5 M solution of n-butyl lithium in n-hexane (1.70 cm3). After ten minutes, a solution of 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl) azetidin-2-one (1.00 g) in dry tetrahydrofuran (15 cm3) was added. Five minutes were allowed for the formation of the C(3) carbanion which was then quenched by the addition of dry acetone (0.71 cm3). The cooling bath was then removed and the mixture stirred for a further ten minutes before it was neutralised with acetic acid (0.56 g). The solvent was evaporated under reduced pressure and the residue chromatographed on silica gel 60 (<230 mesh), eluting with ethyl acetate/60°-80° petroleum ether mixtures grading from 1:1 to 7:3. this gave the two separate isomers of 4-allyl-3-(2-hydroxyprop-2-yl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one(0.30 g 27%) and (0.22 g, 20%); νmax (CHCl3) 3000, 1735 and 1620 cm-1.

Workup

  1. temperaturecooled to -78°
  2. waitAfter ten minutes
  3. customFive minutes
  4. customwas then quenched by the addition of dry acetone (0.71 cm3)
  5. customThe cooling bath was then removed
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue chromatographed on silica gel 60 (<230 mesh)
  8. washeluting with ethyl acetate/60°-80° petroleum ether
  9. customthis gave the two
  10. customseparate isomers of 4-allyl-3-(2-hydroxyprop-2-yl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one(0.30 g 27%) and (0.22 g, 20%)

Sources & evidence

ORD record
ord-87e9a1eb450045e28b13eda5c7f213d8
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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