Acetic Anhydride → HCID 11417634, compound

HRID 1783649Notes

Reaction equation

HRID 1783649 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:15][C@H:16]3[NH:27][CH2:26][CH2:25][C@@:22]4([C:23]=2[CH:24]=1)[C@H:17]3[CH2:18][CH2:19][CH2:20][CH2:21]4.C(N(CC)CC)C>C1COCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:15][C@H:16]3[N:27]([C:1](=[O:3])[CH3:2])[CH2:26][CH2:25][C@@:22]4([C:23]=2[CH:24]=1)[C@H:17]3[CH2:18][CH2:19][CH2:20][CH2:21]4

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1156556936397-14-5

Product 1

HCID 11417634HCID 11417634, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (3.14 g, 30.76 mmol) was added to a solution of (+)-3-methoxy-morphinan hydrochloride (1.5 g, 5.1 mmol) in THF (30 ml) and triethylamine (8.7 g, 85.98 mmol) in the presence of nitrogen. The resulting solution was heated at 60° C. for 15 hr. The reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was dissolved in methylene chloride (50 ml), washed with water (40 ml×2) and dried (MgSO4). Evaporation of the dried solution gave a tan viscous oil (1.25 g, 81% yield); ms (ESI+): m/z 300(M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated under vacuum
  3. dissolutionThe residue was dissolved in methylene chloride (50 ml)
  4. washwashed with water (40 ml×2)
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the dried solution

Sources & evidence

ORD record
ord-d7d00c2b9cdc4c18aaa938fb269d474e
Source dataset
uspto-grants-2009_03
Patent number
US07501433B2

Reaction notes

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