2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 180406-96-6
• Molecular Formula: C₂₁H₃₃NO₄
• Molecular Weight: 363.497
• Mol file: 180406-96-6.mol

Synonyms:2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 3 articles about 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 90.0%

2-(5-benzyloxy-2-oxopentyl)-1-(t-butoxycarbonyl)pyrrolidine (180406-95-5) → 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (180406-96-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 2h; Ambient temperature;

DOI:10.1246/bcsj.69.2063

Reference yield:

5-(benzyloxy)pent-3-yn-2-one (65844-86-2) → 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (180406-96-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Et₃N, NaI / acetonitrile / 8 h / 50 °C

2: 86 percent / CAN, MS 4a / various solvent(s) / 2 h

3: 100 percent / H₂ / 10percent Pd/C / methanol / 5 h / 760 Torr / Ambient temperature

4: 90 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / Ambient temperature

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; hydrogen; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1246/bcsj.69.2063

Reference yield:

(4-Benzyloxy-1-methylene-but-2-ynyloxy)-tert-butyl-dimethyl-silane (180406-85-3) → 2-(5-Benzyloxy-2-hydroxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (180406-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / CAN, MS 4a / various solvent(s) / 2 h

2: 100 percent / H₂ / 10percent Pd/C / methanol / 5 h / 760 Torr / Ambient temperature

3: 90 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / Ambient temperature

With sodium tetrahydroborate; ammonium cerium(IV) nitrate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1246/bcsj.69.2063

upstream raw materials:

2-(5-benzyloxy-2-oxopentyl)-1-(t-butoxycarbonyl)pyrrolidine

5-(benzyloxy)pent-3-yn-2-one

(4-Benzyloxy-1-methylene-but-2-ynyloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

2-(2-Benzoyloxy-5-benzyloxy-pentyl)-pyrrolidine-1-carboxylic acid tert-butyl ester