Dichloromethane → (S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl Ester

HRID 1716536ノート

反応式

HRID 1716536 の反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH:12]=[CH:11]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[BH3-]C#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 20761960(S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl Ester収率 93.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (1.80 g) was dissolved in acetic acid (25 mL) and CH2Cl2 (10 mL) and cooled to 0° C. NaCNBH3 (1.41 g) was added in portions and the resulting mixture was allowed to stir for 4 hours. The reaction mixture was diluted with ethyl acetate and extracted with concentrated NaOH solution. The organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (gradient of ethyl acetate in hexanes) to give the title compound as a brown oil (1.7 g).

後処理

  1. extractionextracted with concentrated NaOH solution
  2. washThe organic layer washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (gradient of ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-eff75cf5657d4db982bad1d17b9ff0d0
出典データセット
uspto-grants-2010_09
特許番号
US07803819B2

反応ノート

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