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

HRID 40842

반응식

HRID 40842 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-369371af84394b78a597fa75f03191d5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530489B2

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