Pyrrolidine → HCID 67246961, compound

HRID 1190915Notes

Reaction equation

HRID 1190915 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:3]=1[CH2:4]OS(C1C=CC(C)=CC=1)(=O)=O.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCOCC1>[F:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:3]=1[CH2:4][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86673337HCID 86673337, compound2×

Product 1

HCID 67246961HCID 67246961, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of toluene-4-sulfonic acid 2-fluoro-5-nitro-benzyl ester (compound of step B of example 29) (0.696 g, 2.31 mmoles) in 1,4-dioxane (20 mL) was added TEA (0.32 mL, 2.31 mmoles) and pyrrolidine (0.19 mL, 2.31 mmoles). The reaction mixture was stirred for 24 h at room temperature, concentrated and purified by TLC (petroleum ether/AcOEt/NH4OH//8/2/0.2). The expected compound was obtained as a yellow oil (0.399 g, 77% yield). MALDI-TOF: m/z 225.1 [M+H]+. 1H NMR (300 MHz, CDCl3) δ8.38; (dd, J=6.2 Hz and 2.9 Hz, 1H), 8.15; (ddd, 4-CH, J=8.9 Hz, 2.9 Hz and 4.4 Hz, 1H), 7.17; (dd, J=8.9 Hz and 8.9 Hz, 1H), 3.76; (s, 2H), 2.5-2.6; (m, 4H), 1.8-1.9; (m, 4H). 13C NMR (75 MHz, CDCl3) δ127.0; (CH, d, J=6.4 Hz), 124.5; (CH, d, J=10.1 Hz), 116.2; (CH, d, J=24.9 Hz), 54.1; (CH2), 52.2; (CH2), 23.5; (CH2).

Workup

  1. concentrationconcentrated
  2. custompurified by TLC (petroleum ether/AcOEt/NH4OH//8/2/0.2)

Sources & evidence

ORD record
ord-c1898a91e0c64946af65335cfc608f72
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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