Hydrochloric Acid → HCID 13851347, compound

HRID 979163Notes

Reaction equation

HRID 979163 reaction equation
C1(PC2C=CC=CC=2)C=CC=CC=1.CO[CH:16]1[C@@H:21]2[C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[O:24][CH2:25][C@@H:20]2[CH2:19][CH2:18][N:17]1[CH2:30][CH2:31][CH3:32].Cl.C1C[O:37]CC1>CCCCCC>[OH:37][C:29]1[C:22]2[C@@H:21]3[C@H:20]([CH2:25][O:24][C:23]=2[CH:26]=[CH:27][CH:28]=1)[CH2:19][CH2:18][N:17]([CH2:30][CH2:31][CH3:32])[CH2:16]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 70017DiphenylphosphineHCID 70427822HCID 70427822, compound

Product 1

HCID 13851347HCID 13851347, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 0.48 g of diphenylphospine in 4 ml THF under nitrogen at 0° is added 1.38 ml n-butylithium (2.24M in hexane). After 3 min., 0.238 g (±)-[4aR*,10bS*]-1,3,4,4a,5,10b-hexahydro-1-methoxy-2-propyl-2 H-[1]benzopyrano[4,3-c]pyridine in 1 ml THF is added. The mixture is refluxed 2.5 hours. After cooling 8 ml 2N HCl is added and the THF evaporated under reduced pressure. The aqueous phase is extracted with two 10 ml portions of ether, basified with solid NaHCO3 and extracted with six 20 ml portions of CH2Cl2. The CH2Cl2 extracts are dried over Na2SO4, filtered, concentrated under reduced pressure and flash chromatographed with CH2Cl2 /ammonia saturated methanol (20:1) to yield the title compound; m.p. of HCl salt 264°-265° dec.

Workup

  1. temperatureThe mixture is refluxed 2.5 hours
  2. additionis added
  3. customthe THF evaporated under reduced pressure
  4. extractionThe aqueous phase is extracted with two 10 ml portions of ether
  5. extractionextracted with six 20 ml portions of CH2Cl2
  6. dry with materialThe CH2Cl2 extracts are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure and flash
  9. customchromatographed with CH2Cl2 /ammonia saturated methanol (20:1)

Sources & evidence

ORD record
ord-55cba402c787463692d1402e26170b47
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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