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

HRID 2261836노트

반응식

HRID 2261836 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-67561306c306470bb7b2adf3a0eea7da
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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