Citric Acid → 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propanol

HRID 1738700Notes

Reaction equation

HRID 1738700 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH2:25][C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[C:30]([C:35]#[N:36])[CH:29]=4)[C:21](OC)=[O:22])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]([CH2:25][C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[C:30]([C:35]#[N:36])[CH:29]=4)[CH2:21][OH:22])=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 56998289HCID 56998289, compound

Product 1

HCID 570293332-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.7 g of methyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(6-cyano-2-indolyl)propionate was dissolved in 30 ml of tetrahydrofuran, followed by the addition of 6606 mg of sodium borohydride. 12 ml of methanol was added dropwise to the thus prepared solution while stirring under ice cooling, and the resulting mixture was stirred at room temperature for 3 hours. The resulting reaction solution was mixed with 10% citric acid aqueous solution, extracted with dichloromethane, and then dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a dichloromethane/methanol mixture as an elution solvent. In this way, 2.2 g of the title compound was obtained in an oily form.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. customThe resulting reaction solution
  3. extractionextracted with dichloromethane
  4. customdried
  5. distillationAfter distilling off the solvent
  6. customthe resulting residue was purified

Sources & evidence

ORD record
ord-76f1d01386624d899ee79c97084c746b
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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