Indoline → tert-Butyl indoline-1-carboxylate

HRID 387240Notes

Reaction equation

HRID 387240 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-5c64f8a4d0c54af5967e7160b91af836
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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