Chloroform → HCID 11566827, compound

HRID 2101650Notes

Reaction equation

HRID 2101650 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:30])[C@H:15]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[CH:16]=[CH:17]/[CH2:18][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:31][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2.C(Cl)(Cl)Cl>CC#N>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:30])[C@H:15]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:16]([F:31])[CH:17]=[CH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 2724933Selectfluor2×HCID 11495484HCID 11495484, compound

Product 1

HCID 11566827HCID 11566827, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one (0.88 mmol, 370 mg) in CH3CN (8 mL) was added [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] (referred to hereafter as Selectfluor) (0.88 mmol, 310 mg). The reaction was allowed to stir at RT for 48 hr. The solvent was removed in vacuo. The crude product was purified by column chromatography to yield a mixture of diastereoisomers de=10% (250 mg, 95%). 1H NMR (400 MHz, CDCl3): δ=6.98-7.3 (m, 10H), 6.0 (m, 1H), 5.5 (dm, J=17, 1H), 5.42 (d, J=10.6, 1H), 5.1 (ddd, J=7.1, 8.1, 47.2, 1H), 4.85 (m, 1H), 4.64 (m, 1H), 3.98-4.12 (m, 2H), 2.84-3.0 (m, 3H), 2.2 (m, 1H); 13C NMR (100 MHz, CDCl3): δ=172.5, 152.9, 137.2, 135.1, 133.7, 133.6, 129.5, 129.3, 128.9, 128.5, 127.2, 126.8, 120.6, 120.5, 94.4 (d, J=175), 65.6, 55.1, 48.1 (d, J=21), 37.3 34.8 (d, J=6); 19F {1H} NMR (376.5 MHz, CDCl3): δ=−175.7; IR (CHCl3): v 3444, 2957, 1645, 1367, 1235, 1205 cm−1; [α]D20=−18.4° (c, 0.5 CHCl3); HMRS required for C22H23NO3F 368.1662 ([M+H+]) found 368.1669.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was purified by column chromatography
  3. customto yield
  4. additiona mixture of diastereoisomers de=10% (250 mg, 95%)

Sources & evidence

ORD record
ord-7f9e18b72a034f79bf345702621bf2de
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

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