Water → 5-(t-butoxycarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

HRID 703540ノート

反応式

HRID 703540 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]1[N:19]([CH3:22])[CH2:20][CH2:21][C:12]21[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si]([N-][Si](C)(C)C)(C)C.[Li+].COS(OC)(=O)=O.O>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]1[N:19]([CH3:22])[CH2:20][CH2:21][C:12]21[CH3:23])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 2733832Lithium HexamethyldisilazideHCID 19908910HCID 19908910、化合物

生成物 1

HCID 199089055-(t-butoxycarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

5-(t-Butyloxycarbonylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (1.7 g) was dissolved in dry THF (15 ml) under nitrogen and cooled to -78° C. in a dry ice/acetone bath. A 1M solution of lithium bis(trimethylsilyl)amide (7.2 ml) in THF was added via a syringe. The solution was stirred at -78° C. for 15 minutes, warmed to room temperature and again cooled to -78° C. before the addition of dimethylsulfate (0.74 g) in THF (5 ml) via syringe. The mixture was stirred for 1 hour and allowed to warm to ambient temperature and water was added in order to quench the reaction. Ethyl acetate (100 ml) was added and the mixture was washed with brine (20 ml), dried (Na2SO4), concentrated and purified by flash chromatography (eluting with 15% MeOH/EtOAc). The pure fractions were concentrated to give 5-(t-butoxycarbonyl-N-methylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (0.42 g).

後処理

  1. temperaturewarmed to room temperature
  2. stirringThe mixture was stirred for 1 hour
  3. temperatureto warm to ambient temperature
  4. customto quench
  5. customthe reaction
  6. washthe mixture was washed with brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (eluting with 15% MeOH/EtOAc)
  10. concentrationThe pure fractions were concentrated

出典と根拠

ORDレコード
ord-06b6bdc7351240b7bb36d6bb8bdde8fb
出典データセット
uspto-grants-1991_01
特許番号
US04983616

反応ノート

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