Acetaldehyde → (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

HRID 1476317노트

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HRID 1476317 반응식
[NH2:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH:16](=O)[CH3:17].[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:20].[Na+]>C(Cl)Cl>[CH2:19]([N:1]([CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:16][CH3:17])[CH3:20]

참가 물질

5

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 44182323(R)-tert-Butyl 3-(aminomethyl)morpholine-4-carboxylate

생성물 1

HCID 66723762(R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A solution of (R)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (commercially available, 250 mg, 1.16 mmol) and DCM (7 ml) at 0° C. was treated with acetaldehyde (0.162 ml, 2.89 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and sodium triacetoxyborohydride (612 mg, 2.89 mmol) was added all at once. The resulting mixture was stirred for 24 h and the mixture was diluted with 20 ml of DCM (20 ml) and washed with saturated aq. sodium bicarbonate (20 ml). The organic phase was dried over sodium sulfate, filtered, and concentrate under pressure to give (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 90, STEP 1)

후처리

  1. stirringThe resulting mixture was stirred for 24 h
  2. washwashed with saturated aq. sodium bicarbonate (20 ml)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate under pressure

출처 및 근거

ORD 기록
ord-125bc16c39aa4681a34f44f25a0295bc
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018381B2

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