Acetic Acid → tert-Butyl(1-benzylpiperidin-3-yl)carbamate, (R)-

HRID 919561ノート

反応式

HRID 919561 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.CC(O)=O.[BH3-]C#N.[Na+].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[CH2:23]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 25417446tert-Butyl(1-benzylpiperidin-3-yl)carbamate, (R)-収率 104%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of (R)-tert-butyl piperidin-3-ylcarbamate (500 mg, 2.4 mmol) in MeOH (15 mL), AcOH (0.75 mL, 12.4 mmol) and NaCNBH3 (310 mg, 4.8 mmol) were added sequentially. To this stirred solution was added benzaldehyde (0.25 mL, 2.4 mmol) drop-wise. The reaction mixture was stirred at rt for 60 h before saturated K2CO3(aq) solution was added to neutralize it. The reaction mixture was concentrated in vacuo to give a residue which was dissolved in water and extracted with EtOAc (30 mL×3). The combined EtOAc layer was dried over Na2SO4 and concentrated in vacuo to afford the titled intermediate (725 mg, 48%) that was used in the next step without further purification. LC-MS: m/z [M+1]=291.

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a residue which
  4. extractionextracted with EtOAc (30 mL×3)
  5. dry with materialThe combined EtOAc layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-aa58ee8b1d06457b93040ae73522b324
出典データセット
uspto-grants-2016_03
特許番号
US09273028B2

反応ノート

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