Hydrochloric Acid → HCID 57497618, compound

HRID 743254Notes

Reaction equation

HRID 743254 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29]COC)[CH:24]=1)=O)(C)(C)C.[ClH:33]>O1CCOCC1>[ClH:33].[OH:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54279493HCID 54279493, compound

Product 1

HCID 57497618HCID 57497618, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

630 mg of (S)-1-t-butoxycarbonyl-2-{2-[2-(3-methoxymethoxyphenyl) ethyl]phenoxymethyl }pyrrolidine [prepared as described in step (a) above] were dissolved in 10 ml of a 4N solution of hydrogen chloride in dioxane, whilst ice-cooling, and the solution was allowed to stand at room temperature for 3 hours. At the end of this time, the mixture was concentrated by distillation under reduced pressure, and the resulting oily residue was dissolved in a small amount of isopropyl alcohol; the solution was then allowed to stand, whilst ice-cooling. The crystals which precipitated were collected by filtration and dried in vacuo, to give 318 mg (yield 66%) of the title compound as colorless crystals, melting at 127°-129° C.

Workup

  1. temperaturecooling
  2. concentrationAt the end of this time, the mixture was concentrated by distillation under reduced pressure
  3. dissolutionthe resulting oily residue was dissolved in a small amount of isopropyl alcohol
  4. temperaturecooling
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-40c6626c0bc24ca882989d4475231063
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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