Borane → HCID 19920953, compound

HRID 1647702Notes

Reaction equation

HRID 1647702 reaction equation
[CH2:1]([NH:5][C:6](=O)[CH2:7][CH2:8][N:9]([CH2:20][CH2:21][C:22](=O)[NH:23][CH2:24][CH2:25][CH2:26][CH3:27])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4].B.C(Cl)Cl>O1CCCC1>[CH2:24]([NH:23][CH2:22][CH2:21][CH2:20][N:9]([CH2:8][CH2:7][CH2:6][NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 6331BoraneHCID 6344DichloromethaneHCID 19920948HCID 19920948, compound

Product 1

HCID 19920953HCID 19920953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve N-butyl-3-[(2-butylcarbamoyl-ethyl)-(toluene-4-sulfonyl)-amino]-propionamide (10 mmol) prepared in example 9, Scheme VI, step C in tetrahydrofuran (50 mL). Cool the solution to 0° C. and add borane (20 mmol, 1M solution in tetrahydrofuran. Heat the reaction to reflux for 18 hours. After cooling, dilute the reaction with methylene chloride (200 mL), rinse with water (100 mL), brine (100 mL), dry over anhydrous sodium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide N,N-bis-(3-butylamino-propyl)-4-methyl-benzenesulfonamide.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 18 hours
  4. temperatureAfter cooling
  5. additiondilute
  6. washrinse with water (100 mL), brine (100 mL)
  7. dry with materialdry over anhydrous sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum
  10. customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-3f10e533c4784100bc80c6894dffb6f6
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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