Water → HCID 20244247, compound

HRID 483010Notes

Reaction equation

HRID 483010 reaction equation
COC1C=C(CNCCCNCCCCNCCCNCC2C=[CH:29][C:28]([OH:31])=[C:27](OC)C=2)C=CC=1O.C(C[CH:39]1[N:44]2[C:45]3[C:50]([CH2:51][CH2:52][CH:43]2[CH2:42][CH2:41][CH2:40]1)=[C:49]([OH:53])[CH:48]=[C:47]([O:54][CH:55]([CH2:57][CH2:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH3:56])[CH:46]=3)(O)=O.[CH3:66][Mg]I.[Cl-].[NH4+].O>C(OCC)C>[OH:53][C:49]1[CH:48]=[C:47]([O:54][CH:55]([CH2:57][CH2:58][CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH3:56])[CH:46]=[C:45]2[C:50]=1[CH:51]([CH2:27][C:28]([OH:31])([CH3:66])[CH3:29])[CH2:52][CH:43]1[CH2:42][CH2:41][CH2:40][CH2:39][N:44]12

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 131713907HCID 131713907, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 20244247HCID 20244247, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 405 mg. (1 mmole) of the lactone of dl-6-carboxymethyl-7-hydroxy-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline, provided in Example 29, in 10 ml. ethyl ether is cooled in an ice bath for 15 minutes. To the cold solution is added slowly by injection 0.80 ml. of 2.9 molar methylmagnesium iodide in ethyl ether. The resulting mixture is allowed to warm to room temperature and stirred for 14 hours. Crystalline ammonium chloride (ca. 100 mg.) is added, the mixture stirred for 20 minutes, water (5 ml.) added and the layers separated. The aqueous layer is extracted with 10 ml. of ether and the combined ether layers are washed with 30 ml. of saturated sodium bicarbonate solution, 30 ml. of brine and 30 ml. of water. The washed organic layer is dried (MgSO4) and solvent evaporated in vacuo to afford the title compound which is purified, if desired, by chromatography.

Workup

  1. additionTo the cold solution is added slowly by injection 0.80 ml
  2. stirringthe mixture stirred for 20 minutes
  3. customthe layers separated
  4. extractionThe aqueous layer is extracted with 10 ml
  5. washof ether and the combined ether layers are washed with 30 ml
  6. dry with materialThe washed organic layer is dried (MgSO4) and solvent
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-495fe1805ddc4fa3b8e296bee5b82cbd
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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