N-Methylbenzylamine → HCID 66998378, compound

HRID 2054828Notes

Reaction equation

HRID 2054828 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:17][C@H:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:25])[C@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22644642tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 66998378HCID 66998378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-3-Methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5.4 g, 25.3 mmol) was dissolved in dichloromethane (75 mL). S-(−)-□-Methylbenzylamine (3.1 g, 3.2 mL, 25.3 mmol) was added followed by sodium triacetoxyborohydride (10.7 g, 50.6 mmol). The reaction was stirred at room temperature overnight. LC/MS analysis revealed four components, with only one component clearly separated. The reaction was diluted with dichloromethane (150 mL) and extracted water (2x), brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to afford a white foam that was purified by flash column chromatography (84.5:15:0.5 dichloromethane:acetonitrile:NH4OH) to afford a clear oil. This material was rechromatographed (89.5:10:0.5 dichloromethane:acetonitrile:NH4OH) to afford the title compound as a clear oil. Wt.: 820 mg (10%). 1H NMR (300 MHz, CDCl3) δ 7.31 (m, 3H), 7.22 (m, 2H), 3.85 (m, 3H), 2.68 (m, 1H), 2.46 (m. 1H), 2.17 (m, 1H), 1.67 (m, 1H), 1.40 (s, 9H), 1.30 (d, 3H), 1.08 (m, 2H), 0.97 (d, 3H); LC/MS m/z 319 (M+H)+.

Workup

  1. customwith only one component clearly separated
  2. additionThe reaction was diluted with dichloromethane (150 mL)
  3. extractionextracted water (2x), brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto afford a white foam that
  8. customwas purified by flash column chromatography (84.5:15:0.5 dichloromethane:acetonitrile:NH4OH)
  9. customto afford a clear oil
  10. customThis material was rechromatographed (89.5:10:0.5 dichloromethane:acetonitrile:NH4OH)

Sources & evidence

ORD record
ord-5bc56aeb614d483b9fa66d17d384cec1
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Reaction notes

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