Formaldehyde → HCID 59428351, compound

HRID 503931Notes

Reaction equation

HRID 503931 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[C:16]([CH3:25])[CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:24][CH2:23][N:22]([CH3:1])[CH2:21]3)=[C:16]([CH3:25])[CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 59428347HCID 59428347, compound

Product 1

HCID 59428351HCID 59428351, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of formaldehyde (37% in water, 1.47 mL, 19.53 mmol) was added to a solution of 3-[4-(4-methoxy-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidine (0.20 g, 0.6301 mmol) in MeOH (2 mL) and the reaction mixture was heated at reflux for 30 minutes. The mixture was cooled to 0° C. and NaBH4 (0.833 g, 22.05 mmol) was slowly added. The mixture was allowed to reach room temperature and it was stirred for an additional hour. The solvent was evaporated under reduced pressure and the residue was partitioned between water and DCM. The organic layer was separated and washed with water and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH) to give 0.167 g (77% yield) of 3-[4-(4-methoxy-benzenesulfonyl)-2-methyl-phenyl]-1-methyl-pyrrolidine as a white foam: MS (M+H)=346.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 30 minutes
  3. customto reach room temperature
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was partitioned between water and DCM
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-dba14d74847046d8a44a947860a906d7
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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