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

HRID 2206588Notes

Reaction equation

HRID 2206588 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+]>>[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

3

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%

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 CH30OH (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-37aa279954154bc9807cdf225236dc3a
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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