APPLICATION
TCI Practical Example: Boc Protection of an Amine Moiety Using Boc2O
Used Chemicals
Indole [I0021]
Di-tert-butyl Dicarbonate (= Boc2O) [D1547]
4-Dimethylaminopyridine (= DMAP) [D1450]
THF
Procedure
To a solution of indole (200 mg, 1.71 mmol) in THF (2 mL) was added DMAP (21 mg, 0.17 mmol, 0.1 eq.) and Boc2O (467 mg, 2.13 mmol, 1.25 eq.) at r.t. and stirred overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (15 mL) and brine (15 mL). Then the organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give N-Boc-indole as a colorless liquid (392 mg, >99% yield).
Experimenter’s Comments
Gas was generated during the reaction.
Analytical Data
N-Boc-indole
1H NMR (270 MHz, CDCl3); δ 8.14 (d, 1H, J = 8.1 Hz), 7.59 (t, 1H, J = 4.1 Hz), 7.57 (d, 1H, J = 7.7 Hz), 7.32 (dt, 1H, J = 6.8, 1.4 Hz), 7.23 (dt, 1H, J = 7.7, 0.8 Hz), 6.58 (d, 1H, J = 4.1 Hz), 1.68 (s, 9H).
Lead Reference/
Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides
M. Chen, Z. Huang, Q. Zheng, Chem. Commun. 2012, 48, 11686.
Application
Selective Protection of Aromatic Amines
PRECAUTIONARY STATEMENTS
P501 : Dispose of contents/ container to an approved waste disposal plant.
P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P262 : Do not get in eyes, on skin, or on clothing.
P240 : Ground/bond container and receiving equipment.
P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking.
P241 : Use explosion-proof electrical/ ventilating/ lighting/ equipment.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P284 : Wear respiratory protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P302 + P350 + P310 : IF ON SKIN: Gently wash with plenty of soap and water. Immediately call a POISON CENTER or doctor/ physician.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P403 + P233 : Store in a well-ventilated place. Keep container tightly closed.
P405 : Store locked up.
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
![Di-tert-butyl Dicarbonate [Boc-reagent for Amino Acid], CAS RN: 24424-99-5, Product Number: D1547](https://content.labscoop.com/products/9cb95b2a-85b6-4161-b205-c67ad9a9c539/CThkFstructure-890-D1547.jpg-Tci-440)
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