Chloroform → HCID 11495484, compound

HRID 2101648Notes

Reaction equation

HRID 2101648 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:25])[C@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]=[CH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([Si:29]([CH3:32])([CH3:31])[CH3:30])C=C.C(Cl)(Cl)Cl>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:25])[C@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[CH:16]=[CH:17]/[CH2:26][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6212Chloroform2×HCID 69808AllyltrimethylsilaneHCID 57801801HCID 57801801, compound

Product 1

HCID 11495484HCID 11495484, compound

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R)-4-benzyl-3-[(2R)-2-benzylbut-3-enoyl]-1,3-oxazolidin-2-one (3.42 mmol, 1.10 g) and allyltrimethylsilane (10.26 mmol, 1.63 mL) in DCM (50 mL) at reflux was added 5 mol % of Grubbs' second generation catalyst (145 mg). After 68 hrs the solvent was removed in vacuo. The crude product was purified by column chromatography to yield a white solid. (1.37 g, 95%); 1H NMR (400 MHz, CDCl3): δ=7.0-7.32 (m, 10H), 5.62 (dt, J=8.1, 15.2, 1H), 5.29-5.36 (m, 1H), 4.82 (m, 1H), 4.61 (m, 1H), 4.01-4.15 (m, 2H), 3.22 (dd, J=8.3, 13.4, 1H), 3.02 (dd, J=3.3, 13.3, 1H), 2.85 (dd, J=6.1, 13.4, 1H), 2.57 (dd, J=9.1, 13.4, 1H) 1.42 (d, J=8.1, 1H) −0.08 (s, 9H); 13C NMR (100 MHz, CDCl3): δ=174.2, 138.9, 135.1, 131.6, 129.4, 128.9, 128.3, 127.2, 126.3, 124.9, 65.7, 55.2, 48.2, 38.9, 37.6, 23.1, −2.1; IR (CHCl3): v 3444, 2955, 1767, 1694, 1454, 1393, 1248, 1182 cm−1; MS (CI(NH3)): m/z 422 (M+H+); HMRS required for C25H32NO3Si ([M]+) 422.2158 found 422.2151; [α]D23=117.8° (c, 0.5 CHCl3); Mp 132-135° C.

Workup

  1. customAfter 68 hrs the solvent was removed in vacuo
  2. customThe crude product was purified by column chromatography
  3. customto yield a white solid

Sources & evidence

ORD record
ord-020dcdf23aac483190c7d878684bfe7b
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

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