Water → Benzyl 2-(1-aminoethyl)morpholine-4-carboxylate

HRID 1527135노트

반응식

HRID 1527135 반응식
[C:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)(=O)[CH3:2].C([O-])(C)=O.[NH4+].[BH3-]C#[N:27].[Na+].O>C1COCC1.CO>[NH2:27][CH:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18354411Phenylmethyl 2-acetyl-4-morpholinecarboxylate

생성물 1

HCID 18354340Benzyl 2-(1-aminoethyl)morpholine-4-carboxylate수율 40%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of benzyl 2-acetylmorpholine-4-carboxylate (5.0 g, 19 mmol) in THF/MeOH (1/5, 100 mL) were added AcONH4 (14.6 g, 190 mmol) and NaBH3CN (11.8 g, 190 mmol). The mixture was stirred at room temperature for 50 hr. The mixture was concentrated to give the crude. Water (20 mL) was added and the mixture was extracted by ethyl acetate (60 mL*3). 1N HCl was added into the combined organic layers. The aqueous layer was concentrated, brought to above pH >8 with 2N NaOH and extracted by ethyl acetate (60 mL*3). The organic layer was washed with brine, dried over sodium sulfate. The mixture was concentrated to give benzyl 2-(1-aminoethyl)morpholine-4-carboxylate (2.0 g, 40%).

후처리

  1. concentrationThe mixture was concentrated
  2. customto give the crude
  3. extractionthe mixture was extracted by ethyl acetate (60 mL*3)
  4. addition1N HCl was added into the combined organic layers
  5. concentrationThe aqueous layer was concentrated
  6. extractionextracted by ethyl acetate (60 mL*3)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe mixture was concentrated

출처 및 근거

ORD 기록
ord-10c0b5c22fcc4dd2a491eeaaeb51f853
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085583B2

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