4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 1-benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-yl-methyl ester

HRID 1013429Notes

Reaction equation

HRID 1013429 reaction equation
C(N(C(C)C)CC)(C)C.CC1C=CN=C(N)C=1C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].[CH2:30]([N:37]1[CH2:41][CH:40]([C:42]2[S:43][CH:44]=[C:45]([Br:47])[CH:46]=2)[CH:39]([CH2:48][OH:49])[CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[CH2:30]([N:37]1[CH2:41][CH:40]([C:42]2[S:43][CH:44]=[C:45]([Br:47])[CH:46]=2)[CH:39]([CH2:48][O:49][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:38]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 110078842-Amino-3,4-dimethylpyridineHCID 58624942[1-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidin-3-yl]-methanol

Product 1

HCID 58624930Toluene-4-sulfonic acid 1-benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-yl-methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (20.2 g, 0.156 mol), dimethyl aminopyridine (320 mg, 2.6 mmol) and TsCl were (9.88 g, 0.052 mol) were added, respectively, to the product of step b) (9.1 g, 0.026 mol) in 150 mL of dichloromethane at 0° C. The reaction mixture was stirred overnight at room temperature and then was quenched with 75 mL of 1 M HCl and extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with brine (100 mL), dried with MgSO4 and evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using a 0-50% methanol-dichloromethane gradient to give the subtitle compound (6.7 g, yield: 51%). MS calculated for C23H24BrNO3S2 +H: 506, observed: 506 and 508.

Workup

  1. additionwere added
  2. customat 0° C
  3. customwas quenched with 75 mL of 1 M HCl
  4. extractionextracted with dichloromethane (3×100 mL)
  5. washThe combined organic extracts were washed with brine (100 mL)
  6. dry with materialdried with MgSO4
  7. customevaporated in vacuo
  8. customto give the crude product that
  9. customwas purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-c59eb45c93e34ec78b0aeee85895ce8a
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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