Ethanol → HCID 11186974, compound

HRID 324880Notes

Reaction equation

HRID 324880 reaction equation
[CH:1]([C:4]1[C:9](C[C@@H](C2C=CC=CC2(O)C)OS(O)(=O)=O)=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:7]([CH2:32][CH2:33][CH3:34])=[C:6]([CH:35]([CH3:37])[CH3:36])[N:5]=1)([CH3:3])[CH3:2].[CH2:38]([OH:40])[CH3:39]>[Ni]>[CH:1]([C:4]1[C:9]([CH:38]([OH:40])[CH3:39])=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:7]([CH2:32][CH2:33][CH3:34])=[C:6]([CH:35]([CH3:36])[CH3:37])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 86756635HCID 86756635, compound

Product 1

HCID 11186974HCID 11186974, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A suspension of Raney nickel (40 g, washed with 3×100 mL ethanol) in ethanol (80 mL) was stirred under hydrogen atmosphere for 1.5 hours. The suspension was treated with a solution of the intermediate obtained in Step B (4.1 g, 8.5 mmol) in ethanol (180 mL) at room temperature and stirred vigorously for 5 hours. The suspension was carefully filtered through celite and concentrated. Filtration through silica gel (CH2Cl2) afforded the title compound (99% e.e.) as a white solid (2.74 g, 8 mmol, 94%). 1H NMR (300 MHz, CDCl3): δ 7.11 (m, 3H), 7.04 (m, 1H), 4.64 (dq, J=3.7, 6.6 Hz, 1H), 3.73 (sept, J=6.6 Hz, 1H), 3.18 (sept,. J=6.6 Hz, 1H), 2.15 (m, 2H), 1.56 (d, J=3.7 Hz, 1H), 1.39 (d, J=6.6 Hz, 3H), 1.28 (m, 14H), 0.73.(t, J=7.35 Hz, 3H). FAB-MS calculated for (C22H31FNO, M+H) 344, found 344. Anal. Calcd for C22H30FNO: C, 76.93; H, 8.80; N, 4.08; F, 5.53; Found: C, 77.20; H, 8.97; N, 4.01; F, 5.60. [a]D=+39.4° (CH2Cl2). mp 104-106° C. Rf=0.4 (CH2Cl2).

Workup

  1. stirringstirred vigorously for 5 hours
  2. filtrationThe suspension was carefully filtered through celite and
  3. concentrationconcentrated
  4. filtrationFiltration through silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-f0a8b38bcb694294a2f8f6816fea05df
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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