N-Methylbenzylamine → HCID 66997280, compound

HRID 2054829Notes

Reaction equation

HRID 2054829 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 66997280HCID 66997280, 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). R-(+)-□-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 overnight at room temperature. LC/MS analysis revealed four components, with only one component clearly separated. The reaction was diluted with dichloromethane (150 mL) and extracted twice with water, once with brine and dried over MgSO4. Filtration and concentration in vacuo afforded a white foam that was purified by flash column chromatography (84.5:15:0.5 CH2Cl2:acetonitrile:NH4OH) to afford a clear oil. The material was rechromatographed (89.5:10:0.5 CH2Cl2:acetonitrile:NH4OH) to afford the title compound as a clear oil. Wt.: 547 mg (7%). 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 twice with water, once with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration in vacuo
  6. customafforded a white foam that
  7. customwas purified by flash column chromatography (84.5:15:0.5 CH2Cl2:acetonitrile:NH4OH)
  8. customto afford a clear oil
  9. customThe material was rechromatographed (89.5:10:0.5 CH2Cl2:acetonitrile:NH4OH)

Sources & evidence

ORD record
ord-ff63ee1e82ef47ada4cfca843151513a
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Reaction notes

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