Pyrrolidine → HCID 22137482, compound

HRID 1827576Notes

Reaction equation

HRID 1827576 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=O)=[CH:19][CH:18]=2)[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:21][CH:22]=2)[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22137375HCID 22137375, compound

Product 1

HCID 22137482HCID 22137482, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-hydroxy-benzyl)-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.093 g, 0.24 mmol) in 1.5 mL methylene chloride was added pyrrolidine (0.034 g, 0.47 mmol) and NaB(OAc)3H (0.092 g, 0.44 mmol). The reaction mixture was stirred at room temperature overnight. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure chromatography (10% methanol/methylene chloride) afforded 0.053 g (50%) of the title compound. MS 451.1 (M+1)+

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0f64b793d39d4481be25f7169ff8b968
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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