4-Nitrobenzenesulfonyl fluoride → 1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-

HRID 2397152Notes

Reaction equation

HRID 2397152 reaction equation
COC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.O=[N+]([O-])c1ccc(S(=O)(=O)F)cc1>C1CCOC1.CN(C)C(=NC(C)(C)C)N(C)C>COC(=O)[C@@H]1C[C@H](F)CN1C(=O)OC(C)(C)C

Participants

5

Reactant 2

HCID 1882464-Nitrobenzenesulfonyl fluorideHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 109777731,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-Yield 40%

Reagents, catalysts & solvents 2

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineReagentHCID 8028TetrahydrofuranSolvent2×

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-126044af69774ff9904328f3b780c561
Source dataset
Deoxyfluorination screen
Original link
View source

Reaction notes

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