Hydroxyamine hydrochloride → tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

HRID 506543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506543
O=[C:2]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.Cl.[NH2:25][OH:26].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[OH:26][N:25]=[C:2]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 49760950Tert-butyl 4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

Produkt 1

HCID 86620083tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-oxo-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate A (1.24 g, 3.93 mmol), hydroxylamine hydrochloride (1.37 g, 19.7 mmol) and sodium acetate trihydrate (3.20 g, 23.5 mmol) in ethanol (50 ml) was heated under reflux for 20 h. The reaction was concentrated and the residue was suspended in water, extracted with dichloromethane (3×). The combined extracts were dried over Na2SO4 and concentrated to give tert-butyl 4-(hydroxyimino)-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate B (1.32 g). LC-MS: m/e=331.1 (M+H, 100%), 275.0 (M+H−C(CH3)3). Rt=3.35 min. 1H-NMR (500 MHz, CDCl3): 8.01 (d, 0.25H), 7.93 (d, 0.75H), 7.41-7.34 (m, 2H), 7.23-7.19 (m, 1H), 3.95-3.92 (m, 2H), 3.04-2.96 (m, 2H), 2.87 (t, 0.5H), 2.82 (t, 1.5H), 2.3 (br. s, 1H), 1.93-1.84 (m, 4H), 1.54-1.52 (d, 2H), 1.43 (s, 9H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. concentrationThe reaction was concentrated
  4. extractionextracted with dichloromethane (3×)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2dd5f4889c0e498197ff422bb844c9fa
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786107B2

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