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

HRID 1916905Notes

Reaction equation

HRID 1916905 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-carboxylate2×

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 (Intermediate (i) obtained above, 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 though 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-e0736f5e272f41018132adc91d0ff34a
Source dataset
uspto-grants-2013_12
Patent number
US08618159B2

Reaction notes

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