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

HRID 2397153Notes

Reaction equation

HRID 2397153 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.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1>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 32%

Reagents, catalysts & solvents 2

HCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneReagentHCID 8028TetrahydrofuranSolvent2×

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-0c7156c1a1f2475c874996afe0b7bca6
Source dataset
Deoxyfluorination screen
Original link
View source

Reaction notes

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