(R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate → tert-Butyl methyl((3R)-piperidin-3-yl)carbamate

HRID 875616노트

반응식

HRID 875616 반응식
[C:1]([O:5][C:6]([N:8]([CH3:25])[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCO.[Pd]>[CH3:25][N:8]([C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 1

HCID 86652138(R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate

생성물 1

HCID 28875356tert-Butyl methyl((3R)-piperidin-3-yl)carbamate수율 82%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

A solution of (R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate (4.00 g, 11.5 mmol) in methanol (10 mL) was slowly added to a suspension of 5% Pd on activated carbon (2.44 g, 1.15 mmol) in EtOH (20 mL). The reaction mixture was evacuated and back filled with N2 (3 cycles). The reaction vessel was then evacuated and back filled with H2 (3 cycles) using a H2 balloon. The mixture was stirred under H2 atmosphere for 1 hour and filtered through a pad of celite, washing with additional 10% MeOH/EtOAc (3×20 mL). The filtrate collected was concentrated in vacuo to provide (R)-tert-butyl methyl(piperidin-3-yl)carbamate (2.01 g, 82% yield) as an oil. LCMS (APCI+) m/z 215 (M+H)+.

후처리

  1. customThe reaction mixture was evacuated
  2. additionback filled with N2 (3 cycles)
  3. customThe reaction vessel was then evacuated
  4. additionback filled with H2 (3 cycles)
  5. filtrationfiltered through a pad of celite
  6. washwashing with additional 10% MeOH/EtOAc (3×20 mL)
  7. customThe filtrate collected
  8. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-f386c62b2c3c45c79c99a5e4f6a1098f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981085B2

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