Sodium borohydride → tert-Butyl 3-(hydroxymethyl)-1H-pyrrolo(2,3-b)pyridine-1-carboxylate

HRID 711297Notes

Reaction equation

HRID 711297 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[C:10]([CH:17]=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[OH:18][CH2:17][C:10]1[C:11]2[C:16](=[N:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118069391-Boc-7-Azaindole-3-carboxaldehyde

Product 1

HCID 49758903tert-Butyl 3-(hydroxymethyl)-1H-pyrrolo(2,3-b)pyridine-1-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-3-formyl-7-azaindole (2.5 g, 10.2 mmol) in 16 mL EtOH was added NaBH4 (115 mg, 3.05 mmol). The reaction was stirred at ambient temperature for 4 h, concentrated and triturated with 1N NaOH. The basic solution was extracted with ether and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The filtrate was concentrated and purified by silica gel chromatography (50% ethylacetate/hexanes) to give tert-butyl 3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (44%). LCMS [M-tert-Bu]+=191.1.

Workup

  1. concentrationconcentrated
  2. customtriturated with 1N NaOH
  3. extractionThe basic solution was extracted with ether and ethylacetate
  4. washThe organics were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe filtrate was concentrated
  9. custompurified by silica gel chromatography (50% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-7b405897180141069aa1cf06be16330f
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

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