1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)-
• CAS No.: 206554-22-5
• Molecular Formula: C17H21NO5
• Molecular Weight: 319.357
• Mol file: 206554-22-5.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)-

There total 5 articles about 1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)- 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: 91.0%

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (206761-38-8) → (3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester (206554-22-5)

Guidance literature:

DOI:10.1021/ol0361507

Reference yield:

(3S,5R)-Piperidine-1,3,5-tricarboxylic acid benzyl ester dimethyl ester (1221818-73-0) → (3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester (206554-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / LiBH₄ / tetrahydrofuran / 45 h / Ambient temperature

2: 78 percent / Pseudomonas fluorescence lipase / 6 h / Ambient temperature

3: Et₃N, SO₃*pyridine / 2 h / 14 °C

With lithium borohydride; pyridine-SO₃ complex; Pseudomonas fluorescence lipase; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo972067j

Reference yield:

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (206761-38-8) → (3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester (206554-22-5) + (3S,5S)-3-Acetoxymethyl-5-formyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:

With pyridine-SO₃ complex; triethylamine; at 14 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo972067j

upstream raw materials:

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

(3S,5R)-Piperidine-1,3,5-tricarboxylic acid benzyl ester dimethyl ester

(3S,5R)-3,5-Bis-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Downstream raw materials:

(3R,5S)-3-carboxyl-5-acetoxymethylpiperidine-1-carboxylic acid benzyl ester

benzyl (3R,5S)-5-acetoxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate

benzyl (3R,5S)-5-hydroxymethyl-3-{[(Z)-1-trimethylsilyl-1-buten-4-yl]carbamoyl}piperidine-1-carboxylate

benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

Refernces

• 1、 Danieli, Bruno,Lesma, Giordano,Passarella, Daniele,Sacchetti, Alessandro,Silvani, Alessandra,Virdis, Andrea. "Total Enantioselective Synthesis of (-)-Cytisine". . p. 493 - 496. Retrieved 2007/10/03.
• 2、 Consonni, Alessandra,Danieli, Bruno,Lesma, Giordano,Passarella, Daniele,Piacenti, Paola,Silvani, Alessandra. "An efficient enantioselective entry to the piperidino-quinolizidine ring system of lupine alkaloids by means of n-acyliminium ion initiated cyclization reactions". . p. 1377 - 1383. Retrieved 2007/10/03.