HCID 67543856, compound → HCID 67545277, compound

HRID 2176118Notes

Reaction equation

HRID 2176118 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](/[CH:11]=[CH:12]\[C:13]1[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[C:6]1[CH2:20][CH:21]3[NH:26][CH:25]([C:5]2=1)[CH2:24][CH2:23][CH2:22]3>CC(O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13]1[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[C:6]1[CH2:20][C@@H:21]3[NH:26][C@H:25]([C:5]2=1)[CH2:24][CH2:23][CH2:22]3

Participants

4

Reactant 1

HCID 67543856HCID 67543856, compound

Product 1

HCID 67545277HCID 67545277, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 2-methyl-5-[(Z)-2-(6-methylpyridin-3-yl)vinyl]-6,7,8,9,10,11-hexahydro-5H-7,11-epiminocycloocta[b]indole (750 mg, 2.18 mmol; from Example 118B) and platinum(IV) oxide (105 mg, 0.462 mmol; Aldrich) in 2-propanol (30 mL) was heated to 65° C. under hydrogen balloon atmosphere (1 atm) for 16 hours, then cooled to room temperature. The catalyst and solvent were removed, and the residue was purified by preparative chiral supercritical fluid chromatography (ChiralPak® OD-H 5 μm column, 21×250 mm, 35° C., 10-50% gradient of CH3OH—CO2 containing 0.1% diethylamine, flow rate 40 mL/minute, 20 minutes) to afford the title compound as the first-eluting enantiomer: 1H NMR (300 MHz, CDCl3) δ ppm 0.96-1.14 (m, J=18, 18, 9, 5 Hz, 1H), 1.25-1.40 (m, 2H), 1.60 (dd, J=13, 2 Hz, 1H), 1.75-1.96 (m, 2H), 2.03 (d, J=17 Hz, 1H), 2.39 (s, 3H), 2.42 (s, 3H), 2.87 (dd, J=17, 7 Hz, 1H), 3.00-3.21 (m, 2H), 3.43 (t, J=6 Hz, 1H), 4.20-4.42 (m, 3H), 6.92 (dd, J=8, 1 Hz, 1H), 7.09-7.15 (m, 2H), 7.20 (d, J=8 Hz, 1H), 7.36 (dd, J=8, 2 Hz, 1H), 7.88 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 346 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customThe catalyst and solvent were removed
  3. customthe residue was purified by preparative chiral supercritical fluid chromatography (ChiralPak® OD-H 5 μm column, 21×250 mm, 35° C., 10-50% gradient of CH3OH—CO2 containing 0.1% diethylamine, flow rate 40 mL/minute, 20 minutes)

Sources & evidence

ORD record
ord-c55070c5673e41cbabe4ec43ab6ee3bb
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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