Water → HCID 70980819, compound

HRID 1475490Notes

Reaction equation

HRID 1475490 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]([OH:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 70980723HCID 70980723, compound

Product 1

HCID 70980819HCID 70980819, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-benzoyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.35 g, 1.0 mmol) in methanol (10 mL) was added sodium borohydride (0.114 g, 3.0 mmol) and the reaction mixture was stirred for 1 hour. Water (5 mL) was added and the reaction mixture was concentrated. Water was added and the product was extracted with EtOAc. The combined organic phase was dried (MgSO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-60% EtOAc in 40-60 petroleum ether) gave the title compound (0.26 g, 73%) as an oil. MS: [M+H]+=355.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionWater was added
  3. extractionthe product was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. customevaporated in vacuo
  6. customto give an oil
  7. washChromatography (SiO2; gradient elution with 0-60% EtOAc in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-4b6bd2ad48cb45a28ae076ba48f7201b
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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