Sodium borohydride → Indopan, (+)-

HRID 1835116Notes

Reaction equation

HRID 1835116 reaction equation
[NH2:1][C@@H:2]([CH3:14])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.[BH4-].[Na+]>C(#N)C.C(O)(C)C>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH2:3][C@@H:2]([NH2:1])[CH3:14])=[CH:6]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12993396(S)-2-amino-1-(1H-indol-3-yl)-propan-1-one

Product 1

HCID 854157Indopan, (+)-

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-2-amino-1-(1H-indol-3-yl)-propan-1-one (0.47 g, 2.5 mmol, 1.0 eq.) in acetonitrile and isopropanol is treated portionwise with NaBH4 (285 mg, 7.49 mmol, 3.0 equiv.), heated at reflux temperature for 24 h, stirred at room temperature under N2 for 36 h, quenched with methanol, concentrated and partitioned between water and EtOAc. The EtOAc phase is dried over MgSO4 and concentrated in vacuo to afford the title product as a brown oil, identified by HPLC and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 24 h
  3. customquenched with methanol
  4. concentrationconcentrated
  5. custompartitioned between water and EtOAc
  6. dry with materialThe EtOAc phase is dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00f191d7c9be496b9dba3aa8cf8d939c
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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