Formaldehyde → 4-(t-Butoxycarbonyl)-1-methylpiperazine-2-carboxamide

HRID 13773노트

반응식

HRID 13773 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:19])[CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylate

생성물 1

HCID 231459204-(t-Butoxycarbonyl)-1-methylpiperazine-2-carboxamide수율 85.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 6.00 g of 4-(t-butoxycarbonyl)piperazine-2-carboxamide and 3.28 g of a 37% aqueous formaldehyde solution in 60 ml of methanol was ice-cooled, and 16.66 g of sodium triacetoxyborohydride was added, followed by stirring at room temperature for 24 hours after removing an ice bath. The reaction solution was again ice-cooled, 3.28 g of a 37% aqueous formaldehyde solution and 16.66 g of sodium triacetoxyborohydride were added thereto. After stirring at room temperature for 16 hours, the reaction solution was diluted with ice water, alkalified with an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate three times. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5.42 g of the objective compound as colorless crystals.

후처리

  1. temperaturecooled
  2. customafter removing an ice bath
  3. temperaturecooled
  4. addition3.28 g of a 37% aqueous formaldehyde solution and 16.66 g of sodium triacetoxyborohydride were added
  5. stirringAfter stirring at room temperature for 16 hours
  6. additionthe reaction solution was diluted with ice water
  7. extractionfollowed by extraction with ethyl acetate three times
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e507ba266287468784932d4566153100
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728131B2

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