Lithium Hydroxide → N-{4-[(S)-1-(3-Hydroxy-propyl)-pyrrolidin-3-yl]-phenyl}-4-isopropyl-benzenesulfonamide

HRID 2262629Notes

Reaction equation

HRID 2262629 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:28]C(=O)C)[CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[OH:28][CH2:27][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][C@@H:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][S:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=3)(=[O:12])=[O:11])=[CH:19][CH:18]=2)[CH2:21]1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 53628668acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl ester

Product 1

HCID 53628667N-{4-[(S)-1-(3-Hydroxy-propyl)-pyrrolidin-3-yl]-phenyl}-4-isopropyl-benzenesulfonamideYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.26 g of acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl ester (0.58 mmol) were dissolved in 4 ml of tetrahydrofuran. 0.021 g lithium hydroxide (0.88 mmol) dissolved in 4 ml water were added and the reaction mixture stirred for 15 h at room temperature. An additional equivalent of lithium hydroxide was added and stirring continued for 24 h before the reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and evaporated to dryness under reduced pressure to yield 0.157 g of the product.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitcontinued for 24 h before the reaction mixture
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4573a096a9c2432fb73785b24159999d
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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