Sodium Bicarbonate → 1-Benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine

HRID 1711393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711393
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][S:25]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26].CC(C)([O-])C.[K+].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[C:18]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxideHCID 588286261-Benzyl-3-(4-nitro-phenoxy)-pyrrolidine

Produkt 1

HCID 588286161-Benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidineAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-benzyl-3-(4-nitro-phenoxy)-pyrrolidine (7.2 g, 24 mmol) and 1-chloromethanesulfonyl-naphthalene (5.8 g, 24 mmol) in THF was chilled in an ice bath, treated dropwise with 1.0 M potassium tert-butoxide in THF (55 mL, 55 mmol), stirred at ambient temperatures for 1 hour, 10 minutes, under nitrogen, poured into water, treated with solid sodium bicarbonate and extracted with ethyl acetate. The extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography using 40-60% ethyl acetate in hexane to give 1-benzyl-3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine as a brown gum/foam, 5.7 g (47.1% yield), Mass spectrum (+EI, [M+H]+) m/z 503. 1HNMR (500 MHz, DMSO-d6): δ8.44-8.46 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.07-8.09 (m, 1H), 7.92-7.96 (m, 2H), 7.58-7.66 (m, 3H), 7.19-7.31 (m, 5H), 6.99 (dd, 1H, J=9.15 Hz and 2.81 Hz), 6.66 (d, 1H, J=2.81 Hz), 5.24 (d, 2H, J=2.20 Hz), 4.65-4.69 (m, 1H), 3.53 (s, 2H), 2.59-2.66 (m, 2H), 2.41-2.42 (m, 1H), 2.27-2.34 (m, 1H), 2.00-2.10 (m, 1H), 1.43-1.54 ppm (m, 1H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-de0ec44cd16143d7b2bf2de8f7f47d64
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790751B2

Notizen zur Reaktion

Wird geladen…