Water → 2-(tert-Butyl)indoline

HRID 468392

Reaction equation

HRID 468392 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CC(O)=O>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 5941662-tert-Butyl-1H-indoleHCID 4311764Sodium borohydride

Product 1

HCID 46426432-(tert-Butyl)indolineYield 116.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-tert-butyl-1H-indole (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10° C. The mixture was stirred for 20 minutes at 10° C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ef6a4cefa9ac48f09e6df065def70b07
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Linked notes

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