Acetic Anhydride → tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

HRID 2386673노트

반응식

HRID 2386673 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17](OC(C)=O)=[O:18]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:17](=[O:18])[CH3:16])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

생성물 1

HCID 66955585tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled suspension of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (15 g) in DCM (300 mL) was added Ac2O (10.8 mL) followed by TEA (2.19 mL), and the resulting mixture was stirred at RT for 3 h. The reaction mixture was then partitioned between DCM and water, and isopropyl amine was added to facilitate the separation. The organic layer was washed with dilute aqueous NaHCO3, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated with Et2O, the solid was collected by filtration and dried under reduced pressure to afford 14.3 g of (4-acetylamino-cyclohexyl)-carbamic acid tert-butyl ester.

후처리

  1. customThe reaction mixture was then partitioned between DCM and water, and isopropyl amine
  2. additionwas added
  3. customthe separation
  4. washThe organic layer was washed with dilute aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with Et2O
  9. filtrationthe solid was collected by filtration
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-3cd38751329c4550b9a29d0e795a8acf
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268840B2

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