1H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-3-oxo-, phenylmethyl ester

Base Information

• Chemical Name: 1H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-3-oxo-, phenylmethyl ester
• CAS No.: 216392-65-3
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.305
• Mol file: 216392-65-3.mol

Synonyms:

Chemical Property of 1H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-3-oxo-, phenylmethyl ester

Chemical Property:

• Vapor Pressure: 6.49E-07mmHg at 25°C
• Boiling Point: 409.5°C at 760 mmHg
• Flash Point: 201.4°C
• PSA: 46.61000
• Density: 1.25g/cm³
• LogP: 1.82270

Purity/Quality:

97% ^*data from raw suppliers

TETRAHYDRO-3-OXO-1H-PYRROLIZINE-7ALPHA(5H)-CARBOXYLIC ACID PHENYLMETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-3-oxo-, phenylmethyl ester

There total 6 articles about 1H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-3-oxo-, phenylmethyl 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:

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → (R)-3-Oxo-tetrahydro-pyrrolizine-7a-carboxylic acid benzyl ester (216392-65-3)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium bis(trimethylsilyl)amide

2: 1.) disiamylborane, 2.) H₂O₂, NaOH

3: Jones reagent

4: H₂ / Pd/C

5: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

6: Ti(O-iPr)4

With titanium(IV) isopropylate; sodium hydroxide; jones reagent; hydrogen; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; palladium on activated charcoal;

DOI:10.1021/ja9815071

Reference yield:

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester (157662-40-3) → (R)-3-Oxo-tetrahydro-pyrrolizine-7a-carboxylic acid benzyl ester (216392-65-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) disiamylborane, 2.) H₂O₂, NaOH

2: Jones reagent

3: H₂ / Pd/C

4: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

5: Ti(O-iPr)4

With titanium(IV) isopropylate; sodium hydroxide; jones reagent; hydrogen; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal;

DOI:10.1021/ja9815071

Reference yield:

(R)-2-(3-Hydroxy-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (848467-63-0) → (R)-3-Oxo-tetrahydro-pyrrolizine-7a-carboxylic acid benzyl ester (216392-65-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Jones reagent

2: H₂ / Pd/C

3: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

4: Ti(O-iPr)4

With titanium(IV) isopropylate; jones reagent; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal;

DOI:10.1021/ja9815071

upstream raw materials:

benzyl alcohol

N-carbobenzyloxy-L-proline methyl ester

(R)-N-(benzoyloxycarbonyl)-allylproline methyl ester

(R)-2-(3-Hydroxy-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

(R)-3-Oxo-tetrahydro-pyrrolizine-7a-carboxylic acid