Sodium Bicarbonate → (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indole

HRID 1440225Notes

Reaction equation

HRID 1440225 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N:27]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=2)[NH:20][CH:19]=1)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:25]=2)[NH:20][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 10414998(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-dibenzylamino-1H-indole

Product 1

HCID 9984453(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indoleYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-dibenzylamino-1H-indole (1.50 g, 2.75 mmol) in anhydrous tetrahydrofuran (30 mL) was added lithium borohydride (0.24 g, 11.0 mmol, 4.0 eq) as a solid. The resulting reaction mixture was heated at reflux for 4 hours. A saturated solution of sodium hydrogen carbonate (10 mL) was then added, and this mixture was stirred at room temperature for 30 minutes. This aqueous mixture was then extracted with ethyl acetate (3×25 mL), and the organic extracts were combined, dried (MgSO4), and evaporated under reduced pressure. Column chromatography of the residue using silica gel (approximately 50 g) and elution with ethyl acetate/hexanes [1:3] afforded the title compound (1.02 g, 70%) as a white foam: FAB LRMS (m/z, relative intensity) 530 (MH+, 87), 529 (M+, 100), 439 (10), 409 (10), 325 (32), 235 (20).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 4 hours
  4. extractionThis aqueous mixture was then extracted with ethyl acetate (3×25 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. washsilica gel (approximately 50 g) and elution with ethyl acetate/hexanes [1:3]

Sources & evidence

ORD record
ord-11c6678a80f746ab9e2ca8dcdfba28fd
Source dataset
uspto-grants-1996_03
Patent number
US05498626

Reaction notes

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