2-Methoxyethylamine → tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

HRID 1842314Notes

Reaction equation

HRID 1842314 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][O:16][CH2:17][CH2:18][NH2:19].[BH4-].[Na+]>CO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][CH2:18][CH2:17][O:16][CH3:15])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Amine preparation: 1-BOC-4-piperidinone (2.00 g) and 2-methoxyethylamine (872 μL) were stirred together in MeOH (20 mL) at room temperature overnight. Sodium borohydride (760 mg) was then added portionwise and the reaction mixture was allowed to stir further at ambient temperature. After 16 h, the solvent was removed in vacuo, the residue was diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester as a colourless oil (1.69 g).

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue was diluted with DCM
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-04956b8faeb94b988df7db2aeb7c3eb4
Source dataset
uspto-grants-2015_02
Patent number
US08946217B2

Reaction notes

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