Hydrochloric Acid → HCID 70623907, compound

HRID 372157Notes

Reaction equation

HRID 372157 reaction equation
B.[CH:2]1([C:6]([N:8]2[CH2:26][CH2:25][C@@:15]34[C:16]5[CH:17]=[C:18]([O:23][CH3:24])[CH:19]=[CH:20][C:21]=5[CH2:22][C@@H:9]2[C@:10]3([OH:28])[CH2:11][CH2:12][C:13](=[O:27])[CH2:14]4)=O)[CH2:5][CH2:4][CH2:3]1.Cl>O1CCCC1>[CH:2]1([CH2:6][N:8]2[CH2:26][CH2:25][C@@:15]34[C:16]5[CH:17]=[C:18]([O:23][CH3:24])[CH:19]=[CH:20][C:21]=5[CH2:22][C@@H:9]2[C@:10]3([OH:28])[CH2:11][CH2:12][C@H:13]([OH:27])[CH2:14]4)[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 57027097HCID 57027097, compound

Product 1

HCID 70623907HCID 70623907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.5 g of borane in 300 ml of tetrahydrofuran (THF) is cooled to -5° under a stream of nitrogen, and then a solution of 35 g of N-cyclobutylcarbonyl-3-methoxy-14-hydroxy-6-ketomorphinan in 200 ml of THF is added slowly over a 45 minute period, keeping the reaction temperature below 0° C. The reaction mixture is then refluxed for 3 hours, cooled, and 150 ml of ZN HCl is added slowly, which induces a vigorous evolution of gas. The solution is then evaporated to a volume of 150 ml in vacuo, diluted with 200 ml of water, and the pH adjusted to 9.0 by the careful addition of 14 N ammonium hydroxide. The precipitate is stirred for two hours and filtered to give crude N-cyclobutylmethyl-3-methoxy-6α,14β-di-hydroxymorphinan.

Workup

  1. customthe reaction temperature below 0° C
  2. temperatureThe reaction mixture is then refluxed for 3 hours
  3. temperaturecooled
  4. customThe solution is then evaporated to a volume of 150 ml in vacuo
  5. additiondiluted with 200 ml of water
  6. additionthe pH adjusted to 9.0 by the careful addition of 14 N ammonium hydroxide
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9a28c96370134eee8bb7d88586425291
Source dataset
uspto-grants-1978_05
Patent number
US04089855

Reaction notes

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