Ammonium Chloride → HCID 21969020, compound

HRID 1420849Notes

Reaction equation

HRID 1420849 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH2:4].[Mg].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[C@@H:20]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C@:21]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH2:4])([OH:25])[C@@H:20]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 5462224MagnesiumHCID 10956740(2S)-1-tert-butoxycarbonyl-2-phenylpiperidin-3-one

Product 1

HCID 21969020HCID 21969020, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A Grignard reagent was prepared from 3-bromo-2-phenylprop-1-ene (Description 93, 150 mg, 0.76 mmol) and magnesium metal (24 mg, 1 mmol) in THF (4 mL). The solution was cooled to -30° C. and a solution of (2S)-1-tert-butoxycarbonyl-2-phenylpiperidin-3-one (Description 1, 161 mg, 0.59 mmol) in THF (1 mL) was added. The mixture was stirred at ambient temperature for 16 h., then saturated aqueous ammonium chloride (10 mL) was added. The mixture was extracted with ethyl acetate (2×20 mL) and the combined organic fractions were dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate (85:15) to give the title compound as an oil (52 mg). 1H NMR (360 MHz, CDCl3) δ7.44-7.20 (10 H, m), 5.43 (1 H, s), 5.25 (1 H, s), 5.12 (1 H, s), 4.06-4.03 (1 H, m), 3.34-3.30 (1 H, m), 3.08-2.94 (3 H, m), 2.47-2.43 (1 H, m), 1.93-1.86 (2 H, m), 1.70-1.64 (2 H, m), and 1.38 (9 H, s). m/z (ES+) 394 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  2. dry with materialthe combined organic fractions were dried (Na2SO4)
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel
  5. washeluting with hexane/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-8fde343837224abf9a9b4f111e23a43d
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

Loading…