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

HRID 1360108Notes

Reaction equation

HRID 1360108 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-tert-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 min and filtered. The filtrate was partitioned between EtOAc and saturated aqueous NaHCO3. The layers were separated and the organic was washed with 1 M HCl, water and brine, dried over Na2SO4, filtered and concentrated. The resulting oil, 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate 23 (4.0 g, 98% yield), 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 were separated
  5. washthe organic was washed with 1 M HCl, water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e3fd6c47e8b4115ad536bd80e16537e
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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