Pyrrolidine → HCID 122496144, compound

HRID 1485636Notes

Reaction equation

HRID 1485636 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]=[S:17](Cl)([CH3:19])=[O:18])(=[O:15])=[O:14])=[CH:9][CH:8]=1>ClCCl.Cl>[CH3:19][S:17](=[N:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=1)(=[O:15])=[O:14])([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 12509526HCID 12509526, compound

Product 1

HCID 122496144HCID 122496144, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyrrolidine (1.53 mL) is added drop wise to N-(4-methylbenzenesulfonyl)methylsulfonimidoyl chloride (5.00 g) in dichloromethane (10 mL) at 0° C. and the resulting mixture is allowed to warm to room temperature overnight. The reaction mixture is diluted with dichloromethane, hydrochloric acid (1 N; 10 mL) is added, and the mixture is stirred for 0.5 h at room temperature. The organic phase is separated, washed with aqueous NaHCO3 solution and water, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 100: 080:20) to give the title compound. LC (method 1): tR=0.88 min; Mass spectrum (ESI+): m/z=303 [M+H]+.

Workup

  1. additionis added
  2. customThe organic phase is separated
  3. washwashed with aqueous NaHCO3 solution and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel (ethyl acetate/methanol 100: 080:20)

Sources & evidence

ORD record
ord-2abd669a5d594403be381902c5065717
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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