Ammonia → HCID 58973516, compound

HRID 409593Notes

Reaction equation

HRID 409593 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.CO[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O.[BH4-].[Na+].N.C1C[O:36][CH2:35]C1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH3:35][O:36][C:29]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:22]([NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:14])=[O:15])=[CH:11][CH:12]=2)[CH2:3]1)[CH3:21]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 776982-Methoxy-1-phenylethanoneHCID 4311764Sodium borohydrideHCID 58973542HCID 58973542, compound

Product 1

HCID 58973516HCID 58973516, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 54 mg of 4-[(S)-3-aminopyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide and 30 mg of 2-methoxyacetophenone in 1 ml of THF was added 85 mg of titanium isopropoxide, and the mixture was stirred at room temperature for 1 day. Further, 12 mg of sodium borohydride was added to the reaction mixture, and then, 0.3 ml of methanol was added to the mixture, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 0.5 ml of 28% aqueous ammonia solution, the mixture was stirred, and then, insoluble materials were removed and the solvent was evaporated. The residue was purified by LC/MS to obtain 61 mg of 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide. The 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide was dissolved by adding 1 ml of tert-butanol, 0.15 ml of 2M aqueous hydrochloric acid was added thereto, and after stirring the mixture, it was freeze-dried to obtain 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide dihydrochloride (the following Table Y, Example 13.001).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. stirringthe mixture was stirred
  3. custominsoluble materials were removed
  4. customthe solvent was evaporated
  5. customThe residue was purified by LC/MS

Sources & evidence

ORD record
ord-43b16af5449144548ac8628e33c6b49d
Source dataset
uspto-grants-2014_06
Patent number
US08759387B2

Reaction notes

Loading…