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 2397147Notes

Reaction equation

HRID 2397147 reaction equation
COC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.O=S(=O)(F)c1ccc(C(F)(F)F)cc1>C1CCOC1.CN1CCCN2CCCN=C12>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 858282354-(Trifluoromethyl)benzenesulfonyl fluoride

Product 1

HCID 109777731,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-rel-Yield 47%

Reagents, catalysts & solvents 2

HCID 1235837-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-eneReagentHCID 8028TetrahydrofuranSolvent2×

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-658ef93b598b456f8fbc467ed3995988
Source dataset
Deoxyfluorination screen
Original link
View source

Reaction notes

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