Morpholine → (1-Methyl-2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester

HRID 340606ノート

反応式

HRID 340606 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:16])[CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH3:16])[CH2:10][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 144271842-tert-Butoxycarbonylaminopropyl methanesulfonate

生成物 1

HCID 15326463(1-Methyl-2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester (23 mmol) in CH3CN (20 mL) was added morpholine (28 mmol) and K2CO3 (23 mmol) at room temperature. The reaction mixture was brought to 50° C. and kept at the same temperature overnight. The reaction mixture was cooled and solvent was removed under reduced pressure, and the residue was treated with CH2Cl2 (50 mL) and H2O (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4. Solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate) to afford (1-methyl-2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester as viscous liquid, yield: 62%. MS (M+H)=245.

後処理

  1. customwas brought to 50° C.
  2. customkept at the same temperature overnight
  3. temperatureThe reaction mixture was cooled
  4. customsolvent was removed under reduced pressure
  5. additionthe residue was treated with CH2Cl2 (50 mL) and H2O (50 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. customSolvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-ff95f8c4c5374b10b7a4992e093fba8f
出典データセット
uspto-grants-2014_11
特許番号
US08895589B2

反応ノート

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