Hydrochloric Acid → HCID 22270492, 화합물

HRID 488607노트

반응식

HRID 488607 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 21226445Aluminium lithium hydrideHCID 858679314-(4-Chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one Oxime

생성물 1

HCID 22270492HCID 22270492, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd2835e88d5a43f2abac0a28586a3edd
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972295B2

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