p-Bromobenzenesulfonyl chloride → 1-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 389188Notes

Reaction equation

HRID 389188 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.C1N2CCN(CC2)C1.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([Br:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>C1(C)C=CC=CC=1>[Br:33][C:32]1[CH:34]=[CH:35][C:29]([S:26]([O:1][C@@H:2]2[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 9237DabcoHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1-t-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.15 g, 8.76 mmol) and DABCO (1.57 g, 14.0 mmol) in PhMe (10 mL) at RT was added a solution of brosyl chloride (3.14 g, 12.3 mmol) in PhMe (5 mL). A white precipitate formed, the reaction mixture was stirred for 20 minutes and filtered. The filtrate was partitioned between EtOAc and saturated aqueous NaHCO3; the layers separated; and the organic phase washed with 1 M HCl, water and brine, dried over Na2SO4, filtered and concentrated to afford the title compound as an oil (4.0 g), which was used without further purification. LRMS (M+Na)+ Calcd.: 488; found 488.

Workup

  1. customA white precipitate formed
  2. filtrationfiltered
  3. customThe filtrate was partitioned between EtOAc and saturated aqueous NaHCO3
  4. customthe layers separated
  5. washand the organic phase washed with 1 M HCl, water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-81aba248ae3740e486747a49d590eece
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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