Indoline → tert-Butyl indoline-1-carboxylate

HRID 656000Notes

Reaction equation

HRID 656000 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>C(Cl)Cl.O>[N:13]1([C:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 10328IndolineHCID 14798Sodium HydroxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 3663954tert-Butyl indoline-1-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of di-tert-butylcarbonate (427.1 g, 1.96 mol) in CH2Cl2 (500 mL) was added dropwise at room temperature to a solution of indoline (212 g 1.78 mol) in CH2Cl2 (1000 mL). A solution of NaOH (85.3 g, 2.13 mol) in water (500 mL) was then added dropwise and the mixture was stirred overnight. The layers were separated and the organic layer was washed with 5% NaOH, brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure and the crude product was crystallized with petroleum ether, giving 324 g (68%) of the title compound.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 5% NaOH, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe crude product was crystallized with petroleum ether

Sources & evidence

ORD record
ord-29f03a9f0a0e423fbab552cf9d5a1602
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

Loading…