Hydrochloric Acid → (+)-5,11-dihydro-5-[[(2R,4R)-4-hydroxy-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine

HRID 365334Notes

Reaction equation

HRID 365334 reaction equation
COC[O:4][C@H:5]1[CH2:9][N:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:7]([CH2:20][N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][O:24][C:23]3[CH:32]=[CH:33][CH:34]=[CH:35][C:22]2=3)[CH2:6]1.Cl>CO>[OH:4][C@H:5]1[CH2:9][N:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:7]([CH2:20][N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][O:24][C:23]3[CH:32]=[CH:33][CH:34]=[CH:35][C:22]2=3)[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15481938(+)-5,11-dihydro-5-[[(2R, 4R)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine

Product 1

HCID 15481939(+)-5,11-dihydro-5-[[(2R,4R)-4-hydroxy-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepineYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.20 g (8.85 mmol) of (+)-5,11-dihydro-5-[[(2R,4R)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine in 40 ml of methanol was treated with 20 ml of 10% HCl for 1 hour under reflux. Methanol was removed in vacuo and 1N NaOH was added to the residue. The products were extracted with ethyl acetate and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silicagel column chromatography (ethyl acetate) to give 3.02 g (79.3%) of (+)-5,11-dihydro-5-[[(2R, 4R)-4-hydroxy-1-(4-methoxyphenethyl)pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine as pale yellow amorphous.

Workup

  1. temperatureunder reflux
  2. customMethanol was removed in vacuo and 1N NaOH
  3. additionwas added to the residue
  4. extractionThe products were extracted with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silicagel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0412dcb42b3a45cb8787a22f18a2905c
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

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