Ethyl Acetate → HCID 86749594, compound

HRID 1733905Notes

Reaction equation

HRID 1733905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[C:10]([N:18]1[CH2:27][CH2:26][C@H:25]2[C@H:20]([CH2:21][CH2:22][C:23](=[O:28])[CH2:24]2)[CH2:19]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>C1COCC1>[C:10]([N:18]1[CH2:27][CH2:26][C@H:25]2[C@H:20]([CH2:21][CH2:22][C:23]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)([OH:28])[CH2:24]2)[CH2:19]1)(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70055598(4aR,8aS)-2-Benzoyloctahydroisoquinolin-6(2H)-oneHCID 178418676HCID 178418676, compound

Product 1

HCID 86749594HCID 86749594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the general procedure described in Example 25, a solution of p-fluorophenyl magnesium bromide in THF (1.0M, 2.61 mL, 2.61 mmol) was reacted with cis-2-benzoyl-6-oxodecahydroisoquinoline (670 mg, 2.61 mmol) in anhydrous THF at -78° C. Column chromatography (ethyl acetate) afforded the product, a solid (478 mg):mp 84°-85° C.; NMR (CDCl3, 200 MHz): 7.5-7.35 (m, 7H), 7.0 (t, 2H, J=8), 4.65-4.35 (m, 1H), 3.8-3.6 (m, 1H), 3.3-3.1 (m, 1H), 3.1-2.8 (m, 1H), 2.65-2.35 (m, 1H), 2.1-1.4 (m, 10 H); Anal. Calcd for C22H24FNO2 : C, 74.76, H, 6.84, N, 3.96, F, 5.38; Found: C, 74.59, H, 6.93, N, 3.79, F, 5.53.

Sources & evidence

ORD record
ord-97c12ffd221741bca350a96e958445db
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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