Borane → HCID 21254052, compound

HRID 1292389Notes

Reaction equation

HRID 1292389 reaction equation
[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

Participants

4

Reactant 2

HCID 6331BoraneHCID 21254076HCID 21254076, compound

Product 1

HCID 21254052HCID 21254052, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2f27c5c55f594c9c92daef52627aad0b
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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