Water → tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1527080Notes

Reaction equation

HRID 1527080 reaction equation
[CH3:1][C:2]1[N:10]([CH:11]([C:13](=[O:15])[CH3:14])[CH3:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH4-].[Na+].O>CO>[OH:15][CH:13]([CH3:14])[CH:11]([N:10]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:2]1[CH3:1])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 89740938HCID 89740938, compound

Product 1

HCID 89740048tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (3.1 g, 10.25 mmol) in methanol (30 mL) was added sodium borohydride (0.30 g, 8.2 mmol) at 0° C. After 30 minutes, another batch of sodium borohydride (0.30 g, 8.2 mmol) was added at 0° C. After the reaction completed about 2 h later, water (30 ml) was added dropwise very carefully to quench the reaction. The mixture was extracted with CH2Cl2. The extraction was dried over Na2SO4, filtered and concentrated under vacuum to give tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a yellow solid. (3.0 g, yield 96%) LCMS (M+H+) m/z: calcd 305.38. found 304.9. 1H NMR (400 MHz, CDCl3): ä 8.31-8.29 (m, 1H), 8.13-8.12 (m, 1H), 7.11-7.07 (m, 1H), 4.46-4.43 (m, 1H), 4.12 (m, 1H), 2.73 (s, 3H), 1.58 (s, 9H), 1.51-1.49 (d, 3H), 0.92-0.91 (d, 3H).

Workup

  1. waitAfter the reaction completed about 2 h
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with CH2Cl2
  5. extractionThe extraction
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-801fdf51bc3f4b1b8891277b2b2b0b6c
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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