Hydrochloric Acid → HCID 22270492、化合物

HRID 30374ノート

反応式

HRID 30374 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10](=[N:12]O)[CH3:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.CCOCC>[ClH:1].[NH2:12][CH:10]([CH:9]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11]

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 21226445Aluminium lithium hydrideHCID 858679314-(4-Chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one Oxime

生成物 1

HCID 22270492HCID 22270492、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

At room temperature, to a solution of 4-(4-chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one oxime (173 mg, 0.648 mmol, from Step C) in 1.8 mL anhydrous THF was added dropwise a 1M solution of lithium aluminum hydride in THF (0.778 mmole). The mixture was refluxed for 20 h. The reaction was quenched by addition of saturated aqueous sodium sulfate (0.1 mL), and stirred overnight. This mixture was filtered over a pad of CELITE diatomaceous earth, and the filtrate was concentrated to dryness. The mass spectrum of this material looked very messy, so the HCl salt was prepared (by addition of a HCl(g) in ether solution) in attempt to clean up the mess. By NMR, the reductive amination provided a ˜1:1 mixture of the two diastereomeric pairs of amines. This HCl salt was rather sticky and difficult to work with and therefore was used in the ensuing coupling experiment without further purification. LC/MS m/e=253 (M+1). 500 MHz 1H NMR (CD3OD) δ 1.56, 1.59 (2 d, J=7.2 Hz, 3H), 2.03 (m, 6H), 2.08 (m, 2H), 3.204.00 (m, 3H), 7.43 (m, 4H)

後処理

  1. temperatureThe mixture was refluxed for 20 h
  2. customThe reaction was quenched by addition of saturated aqueous sodium sulfate (0.1 mL)
  3. filtrationThis mixture was filtered over a pad of CELITE diatomaceous earth
  4. concentrationthe filtrate was concentrated to dryness
  5. customwas prepared (
  6. customBy NMR, the reductive amination provided
  7. customtherefore was used in the ensuing coupling experiment without further purification

出典と根拠

ORDレコード
ord-fa062d37e8464d1095b5c653a0b89413
出典データセット
uspto-grants-2008_09
特許番号
US07423067B2

反応ノート

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