Tetrahydrofuran → (αS)-α-[Bis(phenylmethyl)amino]-4-(trifluoromethyl)benzenepropanal

HRID 2109784노트

반응식

HRID 2109784 반응식
[CH2:1]([N:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[C:10](N(OC)C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOC(C)=O>[CH2:27]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[CH:10]=[O:11])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 21226445Aluminium lithium hydrideHCID 57634048HCID 57634048, 화합물

생성물 1

HCID 57634167(αS)-α-[Bis(phenylmethyl)amino]-4-(trifluoromethyl)benzenepropanal수율 83.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a 500 mL round-bottomed flask was added (S)-2-(dibenzylamino)-N-methoxy-N-methyl-3-(4-(trifluoromethyl)phenyl)propanamide (6.22 g, 13.6 mmol), THF (100 mL), and LAH, 1.0 M solution in THF (27.3 mL, 27.3 mmol), dropwise at 0° C. After 30 minutes, TLC (2:1 hexanes:EtOAc) showed that no starting material remained. The mixture was quenched by dropwise addition of water (6.82 mL), 2 N NaOH (6.82 mL), and water (9.83 mL). The solids were removed by filtration through a medium scintered glass funnel. The filtrate was dried over sodium sulfate and evaporated. The residue was taken up in EtOAc (200 mL) and washed with brine (50 mL). The organic layer was dried over sodium sulfate and evaporated to provide (S)-2-(dibenzylamino)-3-(4-(trifluoromethyl)phenyl)propanal (4.51 g, 83.3% yield) as a light yellow oil. LCMS (ES+) m/z=398.2. 1H NMR (400 MHz, CDCl3) δ ppm 2.96 (dd, J=13.89, 5.67 Hz, 1H) 3.18 (dd, J=13.89, 7.43 Hz, 1H) 3.52-3.55 (m, 1H) 3.66-3.72 (m, 2H) 3.82-3.88 (m, 2H) 7.21-7.33 (m, 12H) 7.50 (d, J=8.02 Hz, 2H) 9.74 (s, 1H).

후처리

  1. customdropwise at 0° C
  2. customThe mixture was quenched by dropwise addition of water (6.82 mL), 2 N NaOH (6.82 mL), and water (9.83 mL)
  3. customThe solids were removed by filtration through a medium
  4. dry with materialThe filtrate was dried over sodium sulfate
  5. customevaporated
  6. washwashed with brine (50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customevaporated

출처 및 근거

ORD 기록
ord-21b84a08982a462b8169041be68dc5f8
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514566B2

반응 노트

불러오는 중…