Sodium borohydride → tert-butyl 1-(3-hydroxypentan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1527075Notes

Reaction equation

HRID 1527075 reaction equation
[CH3:1][C:2]1[N:10]([CH:11]([C:13](=[O:16])[CH2:14][CH3:15])[CH3:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[BH4-].[Na+]>CO>[OH:16][CH:13]([CH2:14][CH3:15])[CH:11]([N:10]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[C:2]1[CH3:1])[CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117778823tert-butyl 2-methyl-1-(3-oxopentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 117778799tert-butyl 1-(3-hydroxypentan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To tert-butyl 2-methyl-1-(3-oxopentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (100 mg, 0.32 mmol) in CH3OH (2 ml) were added NaBH4 (35.9 mg, 0.95 mmol) at 0° C. The mixture was allowed to warm 25° C. with stir for 2 h. After the reaction completed, the solution was concentrated under vacuum and the solid was partitioned between EtOAc and H2O. The organic was separated, dried over Na2SO4 and evaporated under reduced pressure to give tert-butyl 1-(3-hydroxypentan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a white oil. (50 mg yield 50%).

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. customthe solid was partitioned between EtOAc and H2O
  3. customThe organic was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-19e7b8343a43437fa10a9f4144fcefbb
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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