Acetic Acid → 3-[(2-Methoxy-ethyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1689904Notes

Reaction equation

HRID 1689904 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][O:16][CH2:17][CH2:18][NH:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:19]([CH2:18][CH2:17][O:16][CH3:15])[CH3:20])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 300977(2-Methoxyethyl)(methyl)amineHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 574203613-[(2-Methoxy-ethyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl esterYield 81.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Amine preparation: A mixture of 1-BOC-3-piperidone (0.50 g), N-(2-methoxyethyl)methylamine (0.29 g), sodium triacetoxyborohydride (0.74 g) and acetic acid (0.14 mL) in 1,2-dichloroethane (30 mL) was stirred at room temperature for 6 h. The reaction mixture was then diluted with DCM, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 3-[(2-methoxy-ethyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (0.556 g). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.

Workup

  1. washwashed with sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9eee4edcb7ea40138eb77f65d6b3bf31
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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