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

HRID 661113ノート

反応式

HRID 661113 の反応式
[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

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 21226445Aluminium lithium hydrideHCID 57634048HCID 57634048、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-929ac3cd476f42bdb3ba6ed14446f3ec
出典データセット
uspto-grants-2011_12
特許番号
US08084479B2

反応ノート

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