Triethylamine → (S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine

HRID 2251906Notes

Reaction equation

HRID 2251906 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(=O)([O-])O.[Na+]>ClCCl>[CH3:27][S:28]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[CH:10]=2)[CH2:3]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69199429(S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine

Product 1

HCID 86592731(S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-Hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine (1.04 g, 4.00 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (0.76 ml, 5.49 mmol) and methanesulfonyl chloride (0.39 ml, 5.03 mmol) were added to the obtained solution at 0° C. and they were stirred overnight. The reaction mixture was distributed into 5% aqueous sodium hydrogencarbonate solution and dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with chloroform and methanol (95:5), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow oily substance (1.30 g, 96%).

Workup

  1. customThe organic layer was dried
  2. customthe solvent was evaporated under reduced pressure
  3. washAfter the elution with chloroform and methanol (95:5), suitable fractions
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4f2ec73e38447bb8eff78300736474a
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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