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

HRID 2261836ノート

反応式

HRID 2261836 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-67561306c306470bb7b2adf3a0eea7da
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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