Water → HCID 69505881, compound

HRID 618429Notes

Reaction equation

HRID 618429 reaction equation
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].[OH-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CO>[CH2:24]([C:3]1([OH:4])[C:5]2[O:9][C@@H:8]3[C@@:7]45[CH2:21][CH2:20][N:18]([CH3:19])[C@@H:15]([C@@H:14]4[CH:13]=[CH:12][C@@H:10]3[OH:11])[CH2:16][C:17]([C:6]5=2)=[CH:1][CH2:2]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 5288826Morphine

Product 1

HCID 69505881HCID 69505881, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of morphine (14.27 g, 50.0 mmol), NaOH (2.04 g, 51.0 mmol), and benzylbromide (8.47 g, 49.5 mmol) in MeOH (150 ml and water (50 ml) was stirred at rt. for 3.5 hr., evaporated in vacuo to remove MeOH. The residue was extracted with CH2Cl2 (120 ml). The extract was dried over anhydrous Na2SO4 and evaporated in vacuo to dryness to give a crude residue, which was chromatographed on silica gel (column: d=6.5 cm, l=10.5 cm; eluting solvent: 15% MeOH in CH2Cl2) to obtain 3-benzylmorphine (13.1 g, 70% yield). The Rf value in TLC and the IR spectrum of the product were comparable to those obtained from an authentic sample.

Workup

  1. custom, evaporated in vacuo
  2. customto remove MeOH
  3. extractionThe residue was extracted with CH2Cl2 (120 ml)
  4. dry with materialThe extract was dried over anhydrous Na2SO4
  5. customevaporated in vacuo to dryness
  6. customto give a crude residue, which
  7. customwas chromatographed on silica gel (column: d=6.5 cm, l=10.5 cm; eluting solvent: 15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2ef2952a1a9d4fbb966ed19698ff7192
Source dataset
uspto-grants-1999_09
Patent number
US05952495

Reaction notes

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