Ethanolamine → tert-Butyl 4-(2-hydroxyethylamino)piperidine-1-carboxylate

HRID 1162334Notes

Reaction equation

HRID 1162334 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH2:15][CH2:16][CH2:17][OH:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[OH:18][CH2:17][CH2:16][NH:15][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23131007tert-Butyl 4-(2-hydroxyethylamino)piperidine-1-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (15 g), 2-aminoethanol (14 ml), acetic acid (6.6 ml) in 1,2-dichloroethane (300 ml) was mixed at room temperature for 1 hour, and then sodium triacetoxyborohydride (49 g) was added thereto, followed by mixing at room temperature for 15 hours. pH of the aqueous layer was adjusted to about 12 by adding a 1 N aqueous sodium hydroxide solution to the reaction mixture, and then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (18 g, 89%).

Workup

  1. additionby mixing at room temperature for 15 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fabc67f7c47342ea92ab00c5b0d75da7
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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