Triethylamine → Trans-4-hydroxy-3-phthalimidocyclopentene

HRID 543442Notes

Reaction equation

HRID 543442 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH:5]=[CH:4][C@H:3]1[NH2:7].C(N(CC)CC)C.C[O:16][C:17]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])=O>O1CCCC1>[OH:1][C@@H:2]1[CH2:6][CH:5]=[CH:4][C@H:3]1[N:7]1[C:17](=[O:16])[C:19]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:20]2[C:21]1=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11159939Methyl 2-(carbonochloridoyl)benzoateHCID 12943943trans-4-Hydroxy-3-amino-cyclopentene

Product 1

HCID 12943979Trans-4-hydroxy-3-phthalimidocyclopentene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A quantity of dl-trans-4-hydroxy-3-amino-cyclopentene is dissolved in 450 ml of tetrahydrofuran and 87 ml. (0.60 M) of triethylamine. The solution is cooled to 0° and treated dropwise with 59.6 g. (0.3 M) of o-methoxycarbonylbenzoylchloride over 50 min. The reaction is then allowed to warm to 25°. After 66 hours the reaction is partitioned between ethyl acetate and water. The ethyl acetate layer is dried over magnesium sulfate and distilled in vacuo to yield 62.4 g. of residual oil. This is chromatographed over 3 kg. of silica gel 60 eluted with 6 l. of (10-90), 2.5 l. of (15-85), and 11 l. of (20-80) acetonemethylene chloride. Two hundred fifty ml. fractions are collected. The product is found in fractions 38-61. These fractions crystallized on standing to yield 25.9 g. of dl-trans-4-hydroxy-3-phthalidocyclopentene.

Workup

  1. temperatureThe solution is cooled to 0°
  2. additiontreated dropwise with 59.6 g
  3. temperatureto warm to 25°
  4. customAfter 66 hours the reaction is partitioned between ethyl acetate and water
  5. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  6. distillationdistilled in vacuo
  7. customto yield 62.4 g
  8. customThis is chromatographed over 3 kg
  9. washof silica gel 60 eluted with 6 l
  10. customfractions are collected
  11. customThese fractions crystallized
  12. customto yield 25.9 g

Sources & evidence

ORD record
ord-8a2764e298604e5eae0b762135fd6e6f
Source dataset
uspto-grants-1984_05
Patent number
USRE031578

Reaction notes

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