Boron tribromide → HCID 44608136, Verbindung

HRID 1435601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435601
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[CH:11]1[N:16]([CH3:17])[CH2:15][CH2:14][C:13]([CH3:18])=[CH:12]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:17][N:16]1[CH2:15][CH2:14][C:13]([CH3:18])=[CH:12][CH:11]1[C:4]1[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:3]=1[OH:2]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 44610348HCID 44610348, Verbindung

Produkt 1

HCID 44608136HCID 44608136, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2,3,6-tetrahydro-pyridine (6) (300 mg, 1.27 mmol) in dichloromethane (20 ml) cooled at 0° C. under nitrogen was added boron tribromide (3.1 ml, 3.18 mmol of 1.0M solution in dichloromethane), the resultant dark solution was allowed to warm to room temperature and stirred for 1 hour. The solution was poured onto ice and basified with sodium bicarbonate. The layers were separated and the aqueous layer was extracted with dichloromethane (20 ml), the combined organic layers were dried over anhydrous magnesium sulphate, filtered and evaporated to a gum (200 mg). The material was purified on a 10 g silica cartridge eluting with methanol/dichloromethane/ammonia (7:92:1) to yield 4-(1,4-dimethyl-1,2,5,6-tetrahydropyridin-2-yl)-benzene-1,3-diol (8) (93 mg, 35%) as a gum, 1H NMR D6-acetone ??1.67 (s, 3H), 1.97 (m, 1H), 2.3 (s, 3H), 2.42 (m, 1H), 2.74 (m, 1H), 3.08 (m, 1H), 3.74 (s, 1H), 5.15 (s, 1H), 6.2 (d, 1H J=2), 6.27 (dd, 1H J=2.8), 6.82 (d, 1H J=8), 9.4 (bs, 2H).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (20 ml)
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to a gum (200 mg)
  6. customThe material was purified on a 10 g silica cartridge
  7. washeluting with methanol/dichloromethane/ammonia (7:92:1)

Quellen und Nachweise

ORD-Eintrag
ord-3ad062efeff04c93957d289c10dcbdb5
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618966B2

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