Indoline → tert-Butyl indoline-1-carboxylate

HRID 1806193Notes

Reaction equation

HRID 1806193 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10]([O:14][C:15](=O)[O:16]C(C)(C)C)([CH3:13])([CH3:12])[CH3:11]>O1CCCC1>[N:1]1([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

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

Product 1

HCID 3663954tert-Butyl indoline-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indoline (10 g, 84 mmol) was dissolved in tetrahydrofuran (100 mL) and di-tert-butylcarbonate (22 g, 0.1 mol) was added. The mixture was left stirring for 16 hours at room temperature under an inert nitrogen atmosphere. The tetrahydrofuran was removed in vacuo and the crude product purified by vacuum distillation to give the title compound (15.1 g) as a clear pale pink oil that crystallised upon standing (temperature: 160-162° C., pressure 1-0.1 mm Hg).

Workup

  1. waitThe mixture was left
  2. customThe tetrahydrofuran was removed in vacuo
  3. distillationthe crude product purified by vacuum distillation

Sources & evidence

ORD record
ord-6a0bd64bc6314056991bfc49f5a70e18
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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