HCID 66876833, compound → HCID 24984477, compound

HRID 503948Notes

Reaction equation

HRID 503948 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([C@@H:22]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)(C)(C)C>C1COCC1>[CH3:27][N:24]1[CH2:25][CH2:26][C@@H:22]([C:19]2[CH:18]=[CH:17][C:16]([S:13]([C:10]3[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=3)(=[O:15])=[O:14])=[CH:21][CH:20]=2)[CH2:23]1

Participants

3

Reactant 1

HCID 66876833HCID 66876833, compound

Product 1

HCID 24984477HCID 24984477, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of n-tetrabutylammoniumfluoride (1.0 M in THF, 0.593 mL, 0.59 mmol), was added to a solution of (S)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-benzenesulfonyl]-phenyl}-1-methyl-pyrrolidine (242 mg, 0.561 mmol) in THF (2 mL) at 0-5° C. under argon atmosphere. The reaction mixture was stirred at 0-5° C. for 1 hour and then concentrated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH/NH4OH) to give 122 mg of 4-[4-((S)-1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-phenol. The amine (119 mg) was dissolved in isopropanol (2 mL) and was treated with HCl (4 M in 1,4-dioxane, 0.12 mL, 0.487 mL) under nitrogen atmosphere. The mixture was stirred for one hour and the white solid formed was collected by filtration, washed with isopropanol and dried under reduced pressure to give 63 mg of 4-[4-((S)-1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-phenol hydrochloride, MP=197-199° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was purified by preparative TLC (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-88d6287f0a7b4480a159682713c5b6bc
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

Loading…