Hydrochloric Acid → 2-Methyl-[1,3']bipyrrolidinyl hydrochloride

HRID 1516367Notes

Reaction equation

HRID 1516367 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[CH3:18])[CH2:9]1)=O)(C)(C)C.[ClH:19].N#N.[OH-].[K+]>O1CCOCC1.C(Cl)Cl.CO>[ClH:19].[CH3:18][CH:14]1[CH2:15][CH2:16][CH2:17][N:13]1[CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14797Potassium HydroxideHCID 59401804Tert-butyl 3-(2-methylpyrrolidin-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 666245402-Methyl-[1,3']bipyrrolidinyl hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Methyl-[1,3]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester (5.50 g, 21.62 mmol) was treated with 20 mL of 4 M HCl in dioxane at 0° C. The solution was stirred under nitrogen at r.t. overnight. TLC (10% MeOH in DCM) did not detect the starting material. N2 was passed through the solution with stirring. The outlet was passed through KOH solution to absorb HCl for 30 min. The solvent was removed by evaporation to dryness to get the title compound as a hygroscopic gummy material, 5.3 g (˜100%). This material was used without further purification in subsequent steps as illustrated below. LCMS: RT=0.35 minutes, MS: 155 (M+H).

Workup

  1. stirringwith stirring
  2. customto absorb HCl for 30 min
  3. customThe solvent was removed by evaporation to dryness

Sources & evidence

ORD record
ord-2dd96552bbe940f8af877bc70572c1c3
Source dataset
uspto-grants-2012_07
Patent number
US08227481B2

Reaction notes

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