Indoline → tert-Butyl indoline-1-carboxylate

HRID 562005Notes

Reaction equation

HRID 562005 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-16029ddf0a8d469c932ad6bdfbb14bc4
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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