Acetic Acid → HCID 59486385, compound

HRID 1694287Notes

Reaction equation

HRID 1694287 reaction equation
[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

Participants

10

Reactant 6

HCID 176Acetic AcidHCID 947Nitrogen2×HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 426145422-Benzyl-2,7-diazaspiro[4.4]nonaneHCID 67279821(1-Ethylcyclopropyloxy) trimethylsilane

Product 1

HCID 59486385HCID 59486385, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fd3f4e6dac7d443d9a5ed47b54ba3dfe
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

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