Sodium triacetoxyborohydride → 4-{[(2-Fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester

HRID 2261836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261836
[F:1][C:2]1[CH:7]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:19])[C:3]=1[NH:20][CH3:21].[CH3:22][O:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][C:26]=1[CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:22][O:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:20]([C:3]2[C:4]([CH3:19])=[CH:5][C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])=[CH:7][C:2]=2[F:1])[CH3:21])=[CH:27][C:26]=1[CH3:33]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 20134203Methyl 4-formyl-2-methylbenzoateHCID 67528183(2-Fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amine

Produkt 1

HCID 574433494-{[(2-Fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of (2-fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amine (326 mg, 1.05 mmol) and 4-formyl-2-methyl-benzoic acid methyl ester (320 mg, 1.80 mmol) in 4 mL acetic acid is stirred for 2.5 hours at room temperature. Sodium triacetoxyborohydride (773 mg, 3.65 mmol) is added and stirred. Upon completion of the reaction, the mixture is concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer is extracted with ethyl acetate (3×). The combined ethyl acetate layers are dried (MgSO4) and concentrated. The residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 20%) to provide 457 mg (92%) of the titled compound as an oil. MS (ES) m/z 475.3 (M+1).

Aufarbeitung

  1. stirringstirred
  2. customUpon completion of the reaction
  3. concentrationthe mixture is concentrated
  4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer is extracted with ethyl acetate (3×)
  6. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 20%)

Quellen und Nachweise

ORD-Eintrag
ord-67561306c306470bb7b2adf3a0eea7da
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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