Acetic Acid → (2R,5S)-tert-butyl 2-methyl-5-(((R)-3-methylmorpholino)methyl)piperazine-1-carboxylate

HRID 1475482ノート

反応式

HRID 1475482 の反応式
C(O)(=O)C.[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@H:20]2[CH3:25])[N:15](CC2C=CC=CC=2)[CH2:14][C@H:13]1[CH3:33])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CCO.[Pd]>[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@H:20]2[CH3:25])[NH:15][CH2:14][C@H:13]1[CH3:33])=[O:11])([CH3:8])([CH3:6])[CH3:7]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 86724030(2R,5S)-4-Benzyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 70980298(2R,5S)-tert-butyl 2-methyl-5-(((R)-3-methylmorpholino)methyl)piperazine-1-carboxylate収率 95.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Pd/C (33 g) and acetic acid (220 mL) were added to a solution of (2R,5S)-4-benzyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (41.3 g, 102 mmol) in EtOH (300 mL). The mixture was stirred under H2 (1 atmosphere) at room temperature for 18 h. The reaction mixture was then filtered through a pad of Celilte to remove the catalyst and the solvent was removed in vacuo. The crude material was partitioned between saturated aqueous NaHCO3 and DCM and the product extracted with DCM (3×). The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give the title compound (30.5 g) as a pale yellow oil. 1H NMR (CDCl3): 4.43-3.87 (1H, m), 3.78 (1H, d), 3.73-3.55 (3H, m), 3.32 (1H, dd), 3.22 (1H, dd), 3.16-2.93 (3H, m), 2.93-2.72 (1H, m), 2.55-2.35 (2H, m), 2.35-2.15 (2H, m), 1.89 (1H, dd), 1.45 (9H, s), 1.26 (3H, d), 0.96 (3H, d).

後処理

  1. filtrationThe reaction mixture was then filtered through a pad of Celilte
  2. customto remove the catalyst
  3. customthe solvent was removed in vacuo
  4. customThe crude material was partitioned between saturated aqueous NaHCO3 and DCM
  5. extractionthe product extracted with DCM (3×)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3c5aed64360044fda33acce84c0578ff
出典データセット
uspto-grants-2015_04
特許番号
US09018214B2

反応ノート

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