Sodium Iodide → HCID 69429606, compound

HRID 1006785Notes

Reaction equation

HRID 1006785 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][CH2:25]OS(C)(=O)=O)=[O:7])[CH2:2][CH2:3][CH3:4].[NH:31]1[CH:35]=[CH:34][CH:33]=[CH:32]1.[Na+].[I-].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][CH2:25][N:31]1[CH:35]=[CH:34][CH:33]=[CH:32]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8027PyrroleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86584835HCID 86584835, compound

Product 1

HCID 69429606HCID 69429606, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 130 mg (0.257 mmol) (2R,4R)-2-(3-methane-sulfonyloxy-propyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester, 0.037 ml (0.514 mmol) pyrrole and 38.6 mg (0.257 mmol) NaI in 0.4 ml DMF was treated at 0° C. with 22.4 mg (0.514 mmol) 55% NaH and warmed up over night to room temperature. The reaction was neutralized with cooled aqueous saturated NH4Cl and extracted (EtOAc 3×). The organic phase was washed with aqueous 10% NaCl, dried (Na2SO4) evaporated and purified by flash silica gel column (Hexane/EtOAc 9:1) to give 75 mg (68%) of (2R,4R)-4-(4-methoxy-benzylsulfanyl)-2-(3-pyrrol-1-yl-propyl)-pyrrolidine-1-carboxylic acid butyl ester, MS: 431 (MH+).

Workup

  1. extractionextracted (EtOAc 3×)
  2. washThe organic phase was washed with aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. custompurified by flash silica gel column (Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-c716c3071bf349538964fac20a1192c3
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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