HCID 54075037, compound → HCID 67693362, compound

HRID 261103Notes

Reaction equation

HRID 261103 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[N:24](C(OCC(Cl)(Cl)[Cl:30])=O)[CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[ClH:30].[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][C@H:13]3[NH:24][CH2:23][CH2:22][C@@:19]4([C:20]=2[CH:21]=1)[C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18]4)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54075037HCID 54075037, compound

Product 1

HCID 67693362HCID 67693362, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3.4 g (0.007 mol) of (-)-3-phenoxy-N-trichlorocarbethoxymorphinan in 40 ml of 90% acetic acid was added portionwise 2.0 g of zinc-dust. The mixture was stirred at room temperature for 16 hours and filtered. The filtrate was concentrated in vacuo and the residue was partitioned between ether and dilute ammonium hydroxide. The ether solution was extracted with 4 N hydrochloric acid. The acidic solution was extracted with chloroform. After removal of chloroform, the crude hydrochloride was crystallized from ethanol to afford 0.7 g (29%) of (-)-3-phenoxymorphinan hydrochloride, mp 322°-324°, [α]25D-38.88° (c 1.00, MeOH).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was partitioned between ether and dilute ammonium hydroxide
  4. extractionThe ether solution was extracted with 4 N hydrochloric acid
  5. extractionThe acidic solution was extracted with chloroform
  6. customAfter removal of chloroform
  7. customthe crude hydrochloride was crystallized from ethanol

Sources & evidence

ORD record
ord-4d1a6b3eb2e44052b3ed866aa25a79f4
Source dataset
uspto-grants-1979_08
Patent number
US04163853

Reaction notes

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