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

HRID 2365196Notes

Reaction equation

HRID 2365196 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

1-BOC-4-piperidone (2.00 g) and 2-methoxyethylamine (872 μl) were stirred together in methanol (20 ml) at room temperature for 12 hours. Sodium borohydride (760 mg) was added in several aliquots over 30 minutes and the reaction mixture stirred for a further 12 hours at ambient. The solvents were removed in vacuo and the residue diluted with dichloromethane (50 ml) and washed with brine and dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash silica chromatography to give 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.69 g) as a colourless oil.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue diluted with dichloromethane (50 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents were removed in vacuo
  6. customto give a residue which
  7. customwas purified by flash silica chromatography

Sources & evidence

ORD record
ord-679509c52c92426c9acb3f29ca5ee4ff
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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