Acetic Acid → 3,4,5-Trimethyl-piperazine-1-carboxylic acid benzyl ester

HRID 1798550ノート

反応式

HRID 1798550 の反応式
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C=O.[C:21](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH2:12]([O:11][C:9]([N:4]1[CH2:3][CH:2]([CH3:1])[N:7]([CH3:21])[CH:6]([CH3:8])[CH2:5]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23078633Benzyl 3,5-dimethylpiperazine-1-carboxylate

生成物 1

HCID 687346163,4,5-Trimethyl-piperazine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Benzyl 3,5-dimethylpiperazine-1-carboxylate (1 eq, 2.04 mmol, 0.5 g) and formaldehyde (37% in H2O, 5 eq, 10.07 mmol, 0.277 ml) are dissolved in MeOH (10 ml). After 10 mins at room temperature, acetic acid (5 eq, 10.07 mmol, 0.576 ml) and sodium triacetoxyborohydride (5 eq, 10.07 mmol, 2.13 g) are added and the reaction mixture stirred overnight. The reaction is quenched with 5M HCl (15 ml) and the solvent evaporated under vacuo. The residue is taken to pH 13 by addition of sodium hydroxide (4M) and extracted with EtOAc. This organic portion is washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound.

後処理

  1. customThe reaction is quenched with 5M HCl (15 ml)
  2. customthe solvent evaporated under vacuo
  3. additionThe residue is taken to pH 13 by addition of sodium hydroxide (4M)
  4. extractionextracted with EtOAc
  5. washThis organic portion is washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5d93b66ab1ef41348e1c8fa5d822851d
出典データセット
uspto-grants-2013_01
特許番号
US08343966B2

反応ノート

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