1-(4-Methoxybenzene-1-sulfonyl)proline → 1-[(4-Methoxyphenyl)sulfonyl]-2-pyrrolidinemethanol

HRID 352393Notes

Reaction equation

HRID 352393 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[C:17](O)=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:17][OH:18])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 28822671-(4-Methoxybenzene-1-sulfonyl)prolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 52379161-[(4-Methoxyphenyl)sulfonyl]-2-pyrrolidinemethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Part B: To a solution of 4.00 g (14 mmol) of 1-[(4-methoxyphenyl)sulfonyl]-2-carboxypyrrolidine from part A in 50 mL of anhydrous tetrahydrofuran at 0 C under a nitrogen atmosphere, was slowly added over 15 minutes, 20 mL (20 mmol) of a 1M solution of lithium aluminum hydride in diethyl ether. After stirring at room temperature for 2 hours, the solution was cooled in an ice bath, and quenched by the slow sequential addition of 0.8 mL of water, 0.8 mL of 10% sodium hydroxide and 2.4 mL of water. The resulting suspension was filtered through celite and the celite washed with ethyl acetate. The combined organic filtrates were stripped, the residue disolved in ethyl acetate, which was washed with 5% KHSO4, saturated sodium bicarbonate, brine, dried with sodium sulfate, filtered and stripped to afford 3.66 g of crude material. This was chromatographed on 200 g of silica gel using 40%-75% ethyl acetate/hexane to yield pure 1-[(4-methoxyphenyl)sulfonyl]-2-(hydroxymethyl)pyrrolidine, m/e=278 (M+Li).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customquenched by the slow sequential addition of 0.8 mL of water, 0.8 mL of 10% sodium hydroxide and 2.4 mL of water
  3. filtrationThe resulting suspension was filtered through celite
  4. washthe celite washed with ethyl acetate
  5. washthe residue disolved in ethyl acetate, which was washed with 5% KHSO4, saturated sodium bicarbonate, brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customto afford 3.66 g of crude material
  9. customThis was chromatographed on 200 g of silica gel using 40%-75% ethyl acetate/hexane

Sources & evidence

ORD record
ord-01b5c29e8dfe497eaff52a35bc7eef07
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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