Sodium Chloride → HCID 131724596, compound

HRID 1007578Notes

Reaction equation

HRID 1007578 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:16]1([CH3:26])[C:17]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.[Na+].[Cl-]>O.C1(C)C=CC=CC=1>[C:16]1([CH3:26])[C:17]([S:22]([O:13][C@H:10]2[CH2:11][CH2:12][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)(=[O:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8623o-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 131724596HCID 131724596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

(S)-1-Benzyl-3-pyrrolidinol (44.32 g), 132.88 g of toluene and 166.95 g of a 30% aqueous solution of NaOH were respectively weighed and placed in a 500-mL four-necked flask. While the mixture was stirred, the flask inside temperature was lowered to 6.0° C. Then, 104.94 g of toluenesulfonyl chloride was added in divided portions at an interval of about 5 g/10 minutes over 3 hours and 10 minutes at a flask inside temperature of 5 to 10° C. Water (37 mL) was added to dissolve the NaCl which had precipitated out in the aqueous phase, and the mixture was separated into the toluene phase and aqueous phase. A toluene solution of (S)-1-benzyl-3-pyrrolidinol toluenesulfonate was thus obtained in a yield of 85.5 mole percent.

Workup

  1. customplaced in a 500-mL four-necked flask
  2. customwas lowered to 6.0° C
  3. customhad precipitated out in the aqueous phase
  4. customthe mixture was separated into the toluene phase and aqueous phase

Sources & evidence

ORD record
ord-f4848bf022fb4dc295db6f5b0b21d28b
Source dataset
uspto-grants-2004_09
Patent number
US06794519B2

Reaction notes

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