Acetic Anhydride → HCID 21603243, compound

HRID 2166741Notes

Reaction equation

HRID 2166741 reaction equation
[OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21603245HCID 21603245, compound

Product 1

HCID 21603243HCID 21603243, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of (-)-4-hydroxy-N-methylmorphinan-6-one (500 mg, 1.84 mmol), acetic anhydride (5 ml), and pyridine (10 ml) was stirred at room temperature overnight. Acetic anhydride and pyridine were evaporated under vacuum and the residue was taken into toluene and evaporated again. The crude product was taken into CHCl3 and washed with H2O, dried and evaporated to give a foam which was recrystallized from iPr2O-hexane to afford (301 mg, 65%). An analytical sample was recrystallized from iPr2 : mp 96°-97°; [α]D26 -46.7° (c 1.126, CHCl3).

Workup

  1. customAcetic anhydride and pyridine were evaporated under vacuum
  2. customevaporated again
  3. washwashed with H2O
  4. customdried
  5. customevaporated
  6. customto give a foam which
  7. customwas recrystallized from iPr2O-hexane
  8. customto afford (301 mg, 65%)
  9. customAn analytical sample was recrystallized from iPr2

Sources & evidence

ORD record
ord-9a2ed154a97f402aae2b82b4f7e58f1b
Source dataset
uspto-grants-1983_06
Patent number
US04388463

Reaction notes

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