Triethylamine → Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylate

HRID 1959421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959421
[CH2:1]1[C:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]1.CCN(CC)CC.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(Cl)Cl>[C:24]([N:7]1[CH2:6][C:5]2([CH2:1][CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]2)[CH2:9][CH2:8]1)(=[O:27])[CH2:25][CH3:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 23282813tert-Butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate

Produkt 1

HCID 66745092Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of tert-butyl 3,7-diazaspiro[4.4]nonane-3-carboxylate (127 mg, 0.56 mmol) in anhydrous DCM (1 mL), cooled in an ice water bath was added Et3N (57 mg, 78 μL, 0.56 mmol), followed by the addition of propanoyl chloride (57 mg, 54 μL, 0.62 mmol) as a solution in DCM (0.2 mL). The reaction mixture was stirred for 20 minutes, diluted with DCM and was washed with 1M HCl (×2) and brine (×1). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl 3-propanoyl-3,7-diazaspiro[4.4]nonane-7-carboxylate (154 mg, 97%) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 3.73-3.11 (m, 8H), 2.34-2.17 (m, 2H), 1.97-1.70 (m, 4H), 1.46 (s, 9H), 1.16 (t, J=7.4 Hz, 3H). LC/MS m/z 283.5 [M+H]+.

Aufarbeitung

  1. washwas washed with 1M HCl (×2) and brine (×1)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b97e9dcaae534d38b7fecec4fb617833
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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