Lithium iodide → HCID 70046943, compound

HRID 1253300Notes

Reaction equation

HRID 1253300 reaction equation
[OH:1][C:2]1(C(OC)=O)[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:21].[I-].[Li+]>N1C=CC=CC=1>[OH:1][C@H:2]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:21]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 14787654HCID 14787654, compound

Product 1

HCID 70046943HCID 70046943, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution containing 5.26 g (14.6 mmol) of 1,3,4,5-tetrahydro-3-hydroxy-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one and 19. (147 mmol) of anhydrous lithium iodide in 150 ml of dry pyridine was refluxed for one hour. After concentration, the crude product was dissolved in ethyl acetate, washed with 6M hydrochloric acid followed by saturated bicarbonate and dried over sodium sulfate. Concentration followed by trituration with ether gave 2.81 g of essentially pure cis isomer, melting point 173.5°-175.5° C. (dec).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe crude product was dissolved in ethyl acetate
  3. washwashed with 6M hydrochloric acid
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration
  6. customgave 2.81 g of essentially pure cis isomer, melting point 173.5°-175.5° C. (dec)

Sources & evidence

ORD record
ord-15c53738666844c881ee0d44d0570540
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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