Potassium Hydroxide → 1-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene

HRID 380150

Reaktionsgleichung

Reaktionsgleichung von HRID 380150
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][CH:24]2[NH2:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([C:49](=O)[CH2:50][CH2:51][CH:52]=O)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:33][CH:32]=1.[BH3-]C#N.[Na+].[OH-].[K+]>C(O)(=O)C.CO>[CH3:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:38]=[C:39]([CH:49]3[CH2:50][CH2:51][CH2:52][N:29]3[CH:24]3[C:25]4[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:22][CH2:23]3)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:35][CH:36]=1

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 183672311,2,3,4-Tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamineHCID 183673471-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione

Produkt 1

HCID 183672421-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthaleneAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamine (0.21 g), 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.12 g), NaBH3CN (84 mg) and KOH (30 mg) in acetic acid (0.5 ml) and methanol (4 ml). After being stirred for 3 days at room temperature, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[2-[4,5-bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene (0.24 g).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and sat. NaHCO3
  3. washThe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4c38a542bedc46a9aa615bb3bdf6f9bb
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300344B1

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