N-Boc-cis-4-hydroxy-L-proline methyl ester → 1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-

HRID 2397142Notes

Reaction equation

HRID 2397142 reaction equation
COC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.O=S(=O)(F)c1ccccn1>C1CCC2=NCCCN2CC1.C1CCOC1>COC(=O)[C@@H]1C[C@H](F)CN1C(=O)OC(C)(C)C

Participants

5

Reactant 2

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 11615218Pyridine-2-sulfonyl Fluoride

Product 1

HCID 109777731,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-Yield 45%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneReagentHCID 8028TetrahydrofuranSolvent2×

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-9ed322911f41443190312581deb58b8c
Source dataset
Deoxyfluorination screen
Original link
View source

Reaction notes

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