Sodium Iodide → (2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine

HRID 1006783Notes

Reaction equation

HRID 1006783 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][C@H:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][C@H:6]1[CH2:20]OS(C)(=O)=O)(=[O:4])=[O:3].[Na+].[I-].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([NH:35][CH2:20][C@@H:6]1[CH2:7][C@@H:8]([S:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:9][N:5]1[S:2]([CH3:1])(=[O:3])=[O:4])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 87831882(2S,4R)-methanesulfonic acid 1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl ester

Product 1

HCID 69430684(2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amineYield 65%

Procedure

A slurry of 300 mg (0.73 mmol) (2S,4R)-methanesulfonic acid 1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl ester and 109 mg (0.73 mmol) of NaI in 5 ml benzylamine was heated in the oil bath to 100° C., evaporated in the kugelrohr at 50-70° C./1 Torr and extracted with aqueous saturated NaHCO3 solution/Et2O (3×). The organic phase was dried over Na2SO4, evaporated and the residue was crystallized from Et2O/pentane at −20° C. to give 200 mg (65%) of (2S,4R)-benzyl-[1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amine, mp 63-64° C., MS: 421 (MH+).

Workup

  1. customevaporated in the kugelrohr at 50-70° C./1 Torr
  2. extractionextracted with aqueous saturated NaHCO3 solution/Et2O (3×)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. customthe residue was crystallized from Et2O/pentane at −20° C.

Sources & evidence

ORD record
ord-c1726e9e689940f39fa8426bf3e461c7
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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