Borane → HCID 21254052、化合物

HRID 1292389ノート

反応式

HRID 1292389 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[NH:25][C:24]=2[C:33]2[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:20][CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[NH:25][C:24]=2[C:33]2[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 6331BoraneHCID 21254076HCID 21254076、化合物

生成物 1

HCID 21254052HCID 21254052、化合物収率 99.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide(241 mg in 10 mL dry tetrahydrofuran) was added 4 mL of a 1M solution of borane in tetrahydrofuran and the mixture heated slowly to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature and the excess borane quenched by the careful addition of methanol. The mixture was concentrated to half-volume, treated with N,N-dimethylethanolamine (1.4 mL) and heated to reflux on an oil bath. After 3 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 92:8) gave the title compound (234 mg).

後処理

  1. temperaturethe mixture heated slowly
  2. temperatureto reflux on an oil bath
  3. customthe excess borane quenched by the careful addition of methanol
  4. concentrationThe mixture was concentrated to half-volume
  5. additiontreated with N,N-dimethylethanolamine (1.4 mL)
  6. temperatureheated
  7. temperatureto reflux on an oil bath
  8. temperatureAfter 3 hours the mixture was cooled to room temperature
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography on silica gel (methylene chloride:methanol, 92:8)

出典と根拠

ORDレコード
ord-2f27c5c55f594c9c92daef52627aad0b
出典データセット
uspto-grants-1998_05
特許番号
US05756507

反応ノート

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