Dimethylformamide → 4-[(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl]benzaldehyde

HRID 2045903ノート

反応式

HRID 2045903 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:29]=[O:30]>O1CCCC1>[C:16]1([C@H:14]([N:10]2[CH2:11][CH2:12][O:13][C@@H:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:29]=[O:30])=[CH:3][CH:4]=3)[CH2:9]2)[CH3:15])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 50992522(2S)-2-(4-bromophenyl)-4-[(1R)-1-phenylethyl]morpholine2 回HCID 178418339Butyllithium

生成物 1

HCID 593177364-[(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl]benzaldehyde収率 101.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

To a solution of (2S)-2-(4-bromophenyl)-4-((1R)-1-phenylethyl)morpholine (intermediate 7, 63.3 g, 183 mmol) in tetrahydrofuran (450 ml) was added n-butyllithium (1.57 M in hexane solution, 175 ml, 275 mmol) at −78° C. and the mixture was stirred for 20 minutes. N,N-dimethylformamide (28.3 ml 365 mmol) was added and the mixture was stirred for 2 hours at −78° C. and then allowed to be warmed to −10° C. The reaction was quenched with aqueous ammonium chloride, and the resulting solution was partitioned between water and ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford crude 4-((2S)-4-((1R)-1-phenylethyl) morpholin-2-yl)benzaldehyde (intermediate 8, 55.1 g). This compound was used without further purification.

後処理

  1. stirringthe mixture was stirred for 2 hours at −78° C.
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. customthe resulting solution was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-06bb460f06ba4df7a68fb6f5a077a337
出典データセット
uspto-grants-2013_11
特許番号
US08592417B2

反応ノート

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