Diethyl Ether → HCID 73853093, Verbindung

HRID 1245593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245593
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(S([N:41]=[N+:42]=[N-])(=O)=O)=CC=1)CCCCCCCCCCC.C(N(CC)CC)C.CCOCC>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[C:15](=[N+:41]=[N-:42])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109151434-Dodecylbenzenesulfonyl azideHCID 21912749tert-Butyl 4-(3-oxobutanoyl)piperidine-1-carboxylate

Produkt 1

HCID 73853093HCID 73853093, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.51 g (1.8 mmol) of 1-(tert-butoxycarbonyl)-4-(1,3-dioxo-but-1-yl)piperidine (from Step B) and 0.65 g (1.8 mmol) of para-dodecylbenzenesulfonyl azide (Syn. Comm. 1981, 11, 947–956) in CH3CN at 0° C. was treated with 0.26 mL (1.8 mmol) of triethylamine. The reaction was warmed to rt and stirred for 4.5 hours. The reaction was poured into 100 mL of Et2O and washed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified with a 40M Biotage column using 9:1 v/v of hexanes/acetone to afford the title compound as a light yellow oil: RF: 0.33 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.46 (s, 9H), 1.57–1.76 (m, 4H), 2.42 (s, 3H), 2.82 (m, 2H), 3.24 (m, 1H), 4.14 (m, 2H).

Aufarbeitung

  1. washwashed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with a 40M Biotage column

Quellen und Nachweise

ORD-Eintrag
ord-986d0c6234aa46b6ad1b6a02ae87cbc8
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125887B2

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