Hydrochloric Acid → (3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

HRID 906218Notes

Reaction equation

HRID 906218 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([O:11]C(=O)C)[CH2:8][N:7]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[OH:3][CH2:4][C@@H:6]1[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:8][C@@H:9]([OH:11])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15629284(2R,4S)-4-Acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl EsterHCID 21226445Aluminium lithium hydride

Product 1

HCID 15629267(3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 4-acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid ethyl ester (3) (0.65 g, 1.83 mmol) in THF (10 mL) is added LiAlH4 (0.135 g, 3.66 mmol) portion wise. Then the reaction mixture is stirred at room temperature for 1 h. After completion of the reaction, it is cooled to 0° C. and then pH of reaction mixture is adjusted to 3 by adding 6N HCl (0.65 mL). The mixture is concentrated, and the residue is triturated with water (8 mL), the solid precipitated out is filtered, washed with cold water (2×4 mL), and dried under reduced pressure to give compound (4) as white solid.

Workup

  1. customAfter completion of the reaction, it
  2. temperatureis cooled to 0° C.
  3. custompH of reaction mixture
  4. concentrationThe mixture is concentrated
  5. customthe residue is triturated with water (8 mL)
  6. customthe solid precipitated out
  7. filtrationis filtered
  8. washwashed with cold water (2×4 mL)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-5e8b703d5ad64ccea5cba31375c46931
Source dataset
uspto-grants-2011_09
Patent number
US08012983B2

Reaction notes

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