Sodium Hydroxide → (4-(4-Methoxyphenyl)oxan-4-yl)methanamine

HRID 272806노트

반응식

HRID 272806 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:21][NH2:22])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 9751334-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 931713(4-(4-Methoxyphenyl)oxan-4-yl)methanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
7.5 °C

실험 절차

To a stirred suspension of LiAlH4 (79 g, 2.08 mol, 5 eq) in THF (900 ml) at 0 to 5° C. under an atmosphere of nitrogen was added 4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonitrile (90 g, 0.414 mol) in THF (900 ml) over a 25 minutes maintaining the temperature at 5 to 10° C. The reaction mixture was allowed to warm to ambient temperature and stirred until complete. Sodium hydroxide (2N, 850 ml) was added dropwise, the resulting solids filtered and washed with THF (2×800 ml), the organics concentrated in vacuo at 40° C. The residue was dissolved in EtOAc (300 ml) and dried over MgSO4, filtered and concentrated in vacuo at 40° C. to provide {[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-yl]methyl}amine as a light yellow oil (92 g, quantitative).

후처리

  1. temperatureto warm to ambient temperature
  2. filtrationthe resulting solids filtered
  3. washwashed with THF (2×800 ml)
  4. concentrationthe organics concentrated in vacuo at 40° C
  5. dissolutionThe residue was dissolved in EtOAc (300 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo at 40° C.

출처 및 근거

ORD 기록
ord-2f54fc2fc45d430e85012bf053b4ff9d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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