Acetic Acid → HCID 59486385, 화합물

HRID 1694287노트

반응식

HRID 1694287 반응식
[BH3-]C#N.[Na+].[CH2:5]([N:12]1[CH2:16][CH2:15][C:14]2([CH2:20][CH2:19][NH:18][CH2:17]2)[CH2:13]1)[C:6]1[CH:11]=CC=CC=1.C(O)(=O)C.C(C1(O[Si](C)(C)C)CC1)C.C(N)C1C=CC=CC=1.N#N>CO.CCO.[Pd]>[CH:5]1([N:12]2[CH2:16][CH2:15][C:14]3([CH2:20][CH2:19][NH:18][CH2:17]3)[CH2:13]2)[CH2:6][CH2:11]1

참가 물질

10

반응물 6

HCID 176Acetic AcidHCID 947Nitrogen2회HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 426145422-Benzyl-2,7-diazaspiro[4.4]nonaneHCID 67279821(1-Ethylcyclopropyloxy) trimethylsilane

생성물 1

HCID 59486385HCID 59486385, 화합물

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

NaCNBH3 (654 mg, 10.4 mmol) was added to a solution of 2-benzyl-2,7-diaza-spiro[4.4]nonane (450 mg, 2.08 mmol), acetic acid (1.19 ml, 20.8 mmol), molecular sieve (3 Å, beads) and (1-ethylcyclopropyloxy) trimethylsilane (2.09 ml, 10.4 mmol) in MeOH (45 ml) and the mixture was then refluxed. After 4 h the reaction batch was cooled to RT and filtered. The residue was washed with MeOH (50 ml) and the combined organic phases were concentrated to dryness. The residue was taken up in water (5 ml) and NaOH solution (2 M, 10 ml) and extracted with DCM (2×40 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product was used with no further purification. Yield: 440 mg, 82% 2. A solution of benzylamine (440 mg, 1.72 mmol) in absolute EtOH (10 ml) was gassed for 10 min with N2. Then Pd (10% on carbon, 183 mg, 172 μmol) was added and the mixture was again gassed for 10 min with N2. The reaction batch was stirred overnight at RT under an H2 atmosphere (3 bar). On completion of the reaction the mixture was filtered over celite and rewashed with DCM (30 ml) and MeOH (30 ml). The combined filtrates were concentrated to dryness. The product was used without further purification.

후처리

  1. temperaturethe mixture was then refluxed
  2. filtrationfiltered
  3. washThe residue was washed with MeOH (50 ml)
  4. concentrationthe combined organic phases were concentrated to dryness
  5. extractionNaOH solution (2 M, 10 ml) and extracted with DCM (2×40 ml)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe crude product was used with no further purification
  9. customOn completion of the reaction the mixture
  10. filtrationwas filtered over celite
  11. concentrationThe combined filtrates were concentrated to dryness
  12. customThe product was used without further purification

출처 및 근거

ORD 기록
ord-fd3f4e6dac7d443d9a5ed47b54ba3dfe
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158628B2

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