Tetrahydrofuran → Trans-4-hydroxy-3-phthalimidocyclopentene

HRID 543443Notes

Reaction equation

HRID 543443 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.[NH2:12][C@H:13]1[C@H:17]([OH:18])[CH2:16][CH:15]=[CH:14]1.O1CCCC1.C[O:25][C:26]([C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31])=O>C(N(CC)CC)C>[OH:18][C@@H:17]1[CH2:16][CH:15]=[CH:14][C@H:13]1[N:12]1[C:26](=[O:25])[C:28]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:29]2[C:30]1=[O:31]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11159939Methyl 2-(carbonochloridoyl)benzoateHCID 86737601trans-3-Amino-4-hydroxycyclopentene toluenesulfonate

Product 1

HCID 12943979Trans-4-hydroxy-3-phthalimidocyclopentene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 31.3 g. (0.115 M) quantity of dl-trans-3-amino-4-hydroxycyclopentene toluenesulfonate is dissolved in 240 ml. of tetrahydrofuran and 47 ml. (0.46 M) of triethylamine. The resultant stirred solution is cooled to 5° and treated dropwise with 22.8 g. (0.115 M) of o-methoxycarbonylbenzoylchloride. The reaction is then allowed to warm to 25°. After 48 hours the reaction is partitioned between Ethyl acetate and water. The ethyl acetate layer is dried over magnesium sulfate and concentrated in vacuo leaving 29.6 g. of residue. This residue is chromatographed over silica gel 60 eluted with 5 l. of (10-90) and 7.5 l. of (20-80) acetone-methylene chloride. Three hundred ml. fractions are collected. The product is isolated in fractions 25-35, which upon standing crystallizes to yield 14.2 g. of dl-trans-4-hydroxy-3-phthalido-cyclopentene, m.p. 114°-116°.

Workup

  1. temperatureis cooled to 5°
  2. additiontreated dropwise with 22.8 g
  3. temperatureto warm to 25°
  4. customAfter 48 hours the reaction is partitioned between Ethyl acetate and water
  5. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customleaving 29.6 g
  8. customThis residue is chromatographed over silica gel 60
  9. washeluted with 5 l
  10. customfractions are collected
  11. customThe product is isolated in fractions 25-35, which
  12. customupon standing crystallizes
  13. customto yield 14.2 g

Sources & evidence

ORD record
ord-a322be86addb420e8d8536995c249436
Source dataset
uspto-grants-1984_05
Patent number
USRE031578

Reaction notes

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