Acetic Acid → tert-Butyl 4-(benzyl(methyl)amino)piperidine-1-carboxylate

HRID 751654Notes

Reaction equation

C([CH2:8][NH2:9])C1C=CC=CC=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(O[BH-](O[C:34](=O)[CH3:35])OC(=O)C)(=O)C.[Na+].[C:38](O)(=O)C.[CH2:42]1[CH2:46]O[CH2:44][CH2:43]1>>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([N:9]([CH2:8][C:34]2[CH:35]=[CH:46][CH:42]=[CH:43][CH:44]=2)[CH3:38])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

Reactant 5

HCID 176Acetic Acid

HCID 1001Phenethylamine

HCID 8028Tetrahydrofuran

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23292008tert-Butyl 4-(benzyl(methyl)amino)piperidine-1-carboxylate

Procedure

To a solution of N-benzylmethylamine (648 μL, 5.02 mmol) and 1-tert-butoxycarbonyl-4-piperidone (500 mg, 2.51 mmol) in THF (8 mL) was added sodium triacetoxyborohydride (798 mg, 3.76 mmol) followed by acetic acid (144 μL, 2.51 mmol) and the reaction stirred at rt for 40 h. Solvent was removed in vacuo and the residue partitioned between ethyl acetate (15 mL) and water (15 mL). The organic layer was washed with sodium bicarbonate solution (2×15 mL) then brine (2×20 mL), dried (MgSO4) and the solvent removed in vacuo. The crude material was purified by chromatography using ethyl acetate/petroleum ether (2:1) as the eluent to give the title compound as yellow oil. m/z (ES+)=305.32 [M+H]+.

Workup

customSolvent was removed in vacuo
customthe residue partitioned between ethyl acetate (15 mL) and water (15 mL)
washThe organic layer was washed with sodium bicarbonate solution (2×15 mL)
dry with materialbrine (2×20 mL), dried (MgSO4)
customthe solvent removed in vacuo
customThe crude material was purified by chromatography

Sources & evidence

ORD record: ord-580b01d6999b48fdacd94899d2fc52db
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405210B2

Reaction notes

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