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

HRID 875616ノート

反応式

HRID 875616 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f386c62b2c3c45c79c99a5e4f6a1098f
出典データセット
uspto-grants-2015_03
特許番号
US08981085B2

反応ノート

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