Ammonium Acetate → tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

HRID 40842

反応式

HRID 40842 の反応式
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:23].[Na+]>CO.[OH-].[Na+]>[NH2:23][CH:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:2]

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A mixture of tert-butyl 4-acetylpiperidine-1-carboxylate (145 g, 0.64 mol) and ammonium acetate (225 g, 2.9 mol) in methanol (2 L) was stirred at room temperature for 1.5 hours. Sodium cyanoborohydride (30 g, 0.48 mol) was added in one portion and the stirring was continued overnight at room temperature. The reaction mixture was poured in 2N aq. NaOH (2 L) and extracted with dichloromethane (2×1 L). The combined extracts were washed with water (1 L), brine (0.3 L), and evaporated to dryness. The residue was dissolved in TBME (1.5 L), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The residue was purified by bulb to bulb distillation at 180° C. and 0.1 mbar to afford the title compound as a colorless oil that partly solidified upon standing (131 g, 90% yield).

後処理

  1. waitthe stirring was continued overnight at room temperature
  2. extractionextracted with dichloromethane (2×1 L)
  3. washThe combined extracts were washed with water (1 L), brine (0.3 L)
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in TBME (1.5 L)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. distillationThe residue was purified by bulb to bulb distillation at 180° C.

出典と根拠

ORDレコード
ord-369371af84394b78a597fa75f03191d5
出典データセット
uspto-grants-2013_09
特許番号
US08530489B2

関連ノート

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