Piperazin-2-one → 1-Boc-3-(3-oxo-1-piperazinyl)azetidine

HRID 473594

反応式

HRID 473594 の反応式
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][NH:4][CH2:3]1.[C:8]([N:15]1[CH2:18][C:17](=O)[CH2:16]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CC(O)=O>[C:11]([O:10][C:8]([N:15]1[CH2:18][CH:17]([N:4]2[CH2:5][CH2:6][NH:7][C:2](=[O:1])[CH2:3]2)[CH2:16]1)=[O:9])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 3

HCID 231360Piperazin-2-oneHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester2 回HCID 5049666Sodium triacetoxyborohydride2 回

生成物 1

HCID 596054391-Boc-3-(3-oxo-1-piperazinyl)azetidine収率 68.9%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

実験手順

To a mixture of 3-oxopiperazine 4a (490 mg, 4.89 mmol) and N-Boc-azetidin-3-one 1a (922 mg, 5.38 mmol) in 1,2-dichloroethane (10 mL) and HOAc (0.5 mL) was added Na(OAc)3BH (1141, 5.38 mmol). The reaction was stirred at room temperature overnight. Additional 1a (335 mg, 1.96 mmol) and Na(OAc)3BH (415 mg, 1.96 mmol) was added. The reaction was stirred for another 24 h before it was quenched with aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 4% MeOH/CH2Cl2) gave intermediate 4b as white solid (860 mg).

後処理

  1. stirringThe reaction was stirred for another 24 h before it
  2. customwas quenched with aq. NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 4% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-6c6a32182fe444da9fcb8db27933f73c
出典データセット
uspto-grants-2014_01
特許番号
US08637498B2

関連ノート

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