1-Phenethylamine, (+)- → HCID 66997280, compound

HRID 2225063Notes

Reaction equation

HRID 2225063 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].[CH3:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(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:24][C@@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:16])[C@@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6431891-Phenethylamine, (+)-HCID 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-(+)-α-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) δ7.31 (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-3c26bd324cb545c18d5b8a3878917901
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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