Methanesulfonyl chloride → HCID 59643988, compound

HRID 2251903Notes

Reaction equation

HRID 2251903 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][C:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:3]1.C(N(C(C)C)CC)(C)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(=O)([O-])O.[Na+]>ClCCl>[CH3:29][S:30]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)=[CH:11][CH:10]=2)[CH2:3]1)(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 69197702(S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine

Product 1

HCID 59643988HCID 59643988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-Hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine (6.30 g, 23.4 mmol) was dissolved in 100 ml of dichloromethane. Diisopropylethylamine (5.28 ml, 30.0 mmol) and methanesulfonyl chloride (2.34 ml, 30.0 mmol) were added to the obtained solution at 0° C. and they were stirred for 4 hours. 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 dichloromethane and methanol (10:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (S)-3-methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow oily substance (7.50 g, 49%).

Workup

  1. customThe organic layer was dried
  2. customthe solvent was evaporated under reduced pressure
  3. washAfter the elution with dichloromethane and methanol (10:1), suitable fractions
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ad0636d551749e7b3be49dbc53ca8d8
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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