Magnesium → HCID 178521033, compound

HRID 1241510Notes

Reaction equation

HRID 1241510 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C@H:13]3[CH2:16][C@H:15]([CH2:17][O:18]S(C4C=CC(C)=CC=4)(=O)=O)[CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Mg]>CO>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C@H:13]3[CH2:14][C@H:15]([CH2:17][OH:18])[CH2:16]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 178427760HCID 178427760, compound

Product 1

HCID 178521033HCID 178521033, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of: trans-toluene-4-sulfonic acid 3-(4-pyrrolidin-1-ylmethyl-phenyl)-cyclobutylmethyl ester (example 48) (0.5 g, 1.2 mmol) in methyl alcohol (12.5 mL) was added magnesium turning. After 16 hours the reaction turned from a colorless solutions to a milky white solution. The reaction was quenched by the addtion of 1 mL of an aqueous solution of 15% NaOH and water. The solids were filtered off through a plug of celiteand the aqueous layer was extracted with 3:1 CH3Cl:isopropyl alcohol. The combined organic layer were dried over MgSO4, filtered through a fritted funnel and concentrated under reduced pressure to yield the title compound (242 mg, 79% yield) as a colorless oil. This material was processed without further purification.

Workup

  1. customThe reaction was quenched by the addtion of 1 mL of an aqueous solution of 15% NaOH and water
  2. filtrationThe solids were filtered off through a plug of celiteand the aqueous layer
  3. extractionwas extracted with 3:1 CH3Cl
  4. dry with materialThe combined organic layer were dried over MgSO4
  5. filtrationfiltered through a fritted funnel
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4607f0f4c624521a90651c52ac93882
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

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