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Hydrochloric Acid → (3S)-3-(4-Methoxybenzylthio)pyrrolidine hydrochloride

HRID 5089
Notes
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Reaction equation

HRID 5089 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][CH2:12][C@@H:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C.C(OC(C)C)(C)C>[ClH:1].[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][S:14][C@H:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57149914(3R)-1-t-butoxycarbonyl-3-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 14880281(3S)-3-(4-Methoxybenzylthio)pyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

106 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 27.50 g of (3R)-1-t-butoxycarbonyl-3-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (2) above] dissolved in 100 ml of ethyl acetate, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 25° C. for 2 hours. At the end of this time, the mixture was diluted with 200 ml of diisopropyl ether, and the crystals which precipitated were collected by filtration, to give 20.84 g of the title compound as colorless crystals, melting at 125°-126° C.

Workup

  1. waitat 25° C. for 2 hours
  2. customthe crystals which precipitated
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-757ef081a3af49d2a9a2d7813d18eacf
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242914

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes