4-tert-Butylbenzylamine → (4-Tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine

HRID 855177

반응식

HRID 855177 반응식
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=O)[CH2:15][CH2:14]1.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:20][CH2:19][CH:16]2[CH2:17][CH2:18][S:13][CH2:14][CH2:15]2)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 27356554-tert-ButylbenzylamineHCID 4311764Sodium borohydrideHCID 23532962(Tetrahydro-thiopyran-4-YL)-acetaldehyde

생성물 1

HCID 69342005(4-Tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine수율 87%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

0.44 ml of 4-tert-butylbenzylamine (2.5 mmol) and 541 mg (tetrahydro-thiopyran-4-yl)-acetaldehyde (3.75 mmol) were dissolved in 7.5 ml methanol and stirred for 30 min at rt and then refluxed for 2.5 h. After cooling down to rt, 114 mg (3 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was refluxed for 2¾ h. After cooling down to rt, the reaction mixture was treated with 5 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:2 then EtOAc) to give 632 mg light yellow viscous oil (87%). MS (ISP) 292.3 (M+H)+.

후처리

  1. temperaturerefluxed for 2.5 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was refluxed for 2¾ h
  5. temperatureAfter cooling down to rt
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (90 g silica gel

출처 및 근거

ORD 기록
ord-d72b0d96ae2c430e9a02ed5ef497f832
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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