tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate
• CAS No.: 1380347-91-0
• Molecular Formula: C₁₈H₂₂N₄O₄
• Molecular Weight: 358.397
• Mol file: 1380347-91-0.mol

Synonyms:tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate

Chemical Property of tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate

There total 11 articles about tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

2,2,2-trifluoroethyl 3-(1-benzyl-3-nitro-1H-pyrazol-4-yl)-N-(tert-butoxycarbonyl)-L-alaninate (1380347-90-9) → tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate (1380347-91-0)

Guidance literature:

With pyridine; hydrogen; platinum on carbon; for 3h; under 1551.49 Torr;

Reference yield:

(1-benzyl-3-nitro-1H-pyrazol-4-yl)methanol (1380347-81-8) → tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate (1380347-91-0)

Guidance literature:

Multi-step reaction with 6 steps

1: carbon tetrabromide; triphenylphosphine / dichloromethane / 18 h / 20 °C

2: cesiumhydroxide monohydrate; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide / dichloromethane / 18 h / -30 °C

3: trifluoroacetic acid / dichloromethane / 66 h

4: sodium hydroxide / water; tetrahydrofuran / 18 h / 20 °C

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 18 h

6: hydrogen; pyridine / platinum on carbon / 3 h / 1551.49 Torr

With pyridine; cesiumhydroxide monohydrate; carbon tetrabromide; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; dmap; platinum on carbon; In tetrahydrofuran; dichloromethane; water;

Reference yield:

1-benzyl-4-(bromomethyl)-3-nitro-1H-pyrazole (1380347-82-9) → tert-butyl [(5S)-2-benzyl-7-hydroxy-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-5-yl]carbamate (1380347-91-0)

Guidance literature:

Multi-step reaction with 5 steps

1: cesiumhydroxide monohydrate; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide / dichloromethane / 18 h / -30 °C

2: trifluoroacetic acid / dichloromethane / 66 h

3: sodium hydroxide / water; tetrahydrofuran / 18 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 18 h

5: hydrogen; pyridine / platinum on carbon / 3 h / 1551.49 Torr

With pyridine; cesiumhydroxide monohydrate; O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium hydroxide; dmap; platinum on carbon; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

tert-butyl 3-(1-benzyl-3-nitro-1H-pyrazol-4-yl)-N-(diphenylmethylene)-L-alaninate

3-(1-benzyl-3-nitro-1H-pyrazol-4-yl )-N-(tert-butoxycarbonyl )-Lalanine

2,2,2-trifluoroethyl 3-(1-benzyl-3-nitro-1H-pyrazol-4-yl)-N-(tert-butoxycarbonyl)-L-alaninate

ethyl 1-benzyl-3-nitro-1H-pyrazole-4-carboxylate

Downstream raw materials:

(5S)-5-amino-2-benzyl-7-hydroxy-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one