Hexane → HCID 58630654, compound

HRID 2376205Notes

Reaction equation

HRID 2376205 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.[I-].ClC1C=CC=C[N+]=1C.[O:21]1[C@@H:25]2[CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[C@@H:24]2[NH:23][C:22]1=[O:33].CCCCCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([N:23]2[C@H:24]3[C:32]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH2:26][C@H:25]3[O:21][C:22]2=[O:33])=[O:10])[CH:2]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 12121m-Tolylacetic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 10954036(3aS-cis)-(-)-3,3a,8,8a-Tetrahydro-2H-indeno[1,2-d]oxazol-2-one

Product 1

HCID 58630654HCID 58630654, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of m-tolylacetic acid (8.57 g, 0.0571 mol), 2-chloro-1-methylpyridinium iodide (19.0 g, 0.0744 mol) and (3aS-cis)-(−)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]-oxazol-2-one (10.0 g, 0.0571 mol) in CH2Cl2 (130 mL) were added TEA (18.0 mL, 0.129 mol) and 4-dimethylaminopyridine (DMAP, 1.39 g, 0.0114 mol) at 0° C. The reaction mixture was stirred at rt for 3 h then treated with hexane (130 mL). The resulting slurry was passed through a pad of silica gel, eluting with 3:2 EtOAc/hexane. The filtrate was concentrated to an oil and recrystallized in hot hexane to recover 13 g (74%) of the title compound as a white solid. HPLC: Rt=9.85 (Method E). MS (ES+): mass calculated for C19H17NO3, 307.36; m/z found 330.2 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.65 (d, J=7.6 Hz, 1H), 7.08-7.37 (m, 7H), 5.95 (d, J=6.8 Hz, 1H), 5.27-5.31 (m, 1H), 4.26 (dd, J=15.9, 39.1 Hz, 2H), 3.40 (d, J=3.5 Hz, 2H), 2.34 (s, 3H).

Workup

  1. washeluting with 3:2 EtOAc/hexane
  2. concentrationThe filtrate was concentrated to an oil
  3. customrecrystallized in hot hexane
  4. customto recover 13 g (74%) of the title compound as a white solid

Sources & evidence

ORD record
ord-ea8b9a61917445ab8b579edb887f484b
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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