1-Naphthaldehyde → (S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine

HRID 1254489

반응식

HRID 1254489 반응식
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].[C:11]1([CH:21]=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:21][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:6])[CH3:2]

참가 물질

6

반응물 3

HCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12398111(2S)-1,1-Diethoxy-2-propanamine

생성물 1

HCID 67075196(S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine수율 67.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To the solution of (S)-1,1-diethoxypropan-2-amine (Compound XIX-1) 682 mg (3.55 mmol) in tetrahydrofuran 2 ml, 1-naphthaldehyde 554 mg (3.55 mmol) was added and stirred at room temperature for 0.5 hour. The reaction mixture was diluted with tetrahydrofuran 3 ml and sodium triacetoxyborohydride 829 mg (3.91 mmol) was added and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated sodium bicarbonate aq. 50 ml twice, water 50 ml twice and brine 50 ml twice. The organic phase was dried with magnesium sulfate and filtered and the mother solution was concentrated in vacuo to obtain the title compound 685 mg (67.1%).

후처리

  1. additionwas added
  2. stirringstirred at room temperature for 18 hours
  3. washwashed with saturated sodium bicarbonate aq. 50 ml twice
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe mother solution was concentrated in vacuo

출처 및 근거

ORD 기록
ord-a4667eb89f334e58b4fe84db0cc95cb3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455488B2

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