Acetic Acid → (S)-Tert-butyl 4-methyl-4-(3-methylpiperazin-1-YL)piperidine-1-carboxylate

HRID 2387455ノート

反応式

HRID 2387455 の反応式
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2([CH3:27])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH2:10][C@@H:9]1[CH3:28])C1C=CC=CC=1.C(O)(=O)C>CO>[CH3:27][C:14]1([N:11]2[CH2:12][CH2:13][NH:8][C@@H:9]([CH3:28])[CH2:10]2)[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 176Acetic AcidHCID 59017283t-Butyl 4-[(3S)-4-Benzyl-3-methylpiperazin-1-yl]-4-methylpiperidine-1-carboxylate

生成物 1

HCID 17759466(S)-Tert-butyl 4-methyl-4-(3-methylpiperazin-1-YL)piperidine-1-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of t-butyl 4-[(3S)-4-benzyl-3-methylpiperazin-1-yl]-4-methylpiperidine-1-carboxylate (45.5 g, 0.118 mol) in methanol (320 mL) and acetic acid (35 mL, 5 equiv) in a 2.25 L Parr bottle was charged with H2 to 60 psi and the mixture shaken for 18 hr. The reaction mixture was filtered through a pad of Celite and the pad was washed with methanol. The filtrate was concentrated under vacuum. The residual oil was dissolved in DCM (500 mL) and washed with aqueous sodium hydroxide (300 mL). The aqueous phase was back-extracted with methylene chloride (200 mL). The combined organic solution was washed with brine (500 mL), dried with sodium sulfate and the solvent was removed under vacuum to give 35 g (100%) of product as a pale yellow viscous oil that slowly crystallized. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.44 (m, 2H), 3.36 (m, 2H), 2.97 (dt, 1H), 2.84 (dd, 1H), 2.78 (m, 1H), 2.71 (brd, 2H), 2.16 (dt, 1H), 1.81 (t, 2H), 1.76 (m, 1H), 1.45 (s, 9H), 1.34 (m, 3H), 1.03 (d, 3H), 0.90 (s, 3H); MS (EI) 298.2 (M+1).

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe pad was washed with methanol
  3. concentrationThe filtrate was concentrated under vacuum
  4. dissolutionThe residual oil was dissolved in DCM (500 mL)
  5. washwashed with aqueous sodium hydroxide (300 mL)
  6. extractionThe aqueous phase was back-extracted with methylene chloride (200 mL)
  7. washThe combined organic solution was washed with brine (500 mL)
  8. dry with materialdried with sodium sulfate
  9. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-f3c761fd26e94df1a719be5b040d88d7
出典データセット
uspto-grants-2012_09
特許番号
US08268826B2

反応ノート

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