(+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one

Base Information

• Chemical Name: (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one
• CAS No.: 134037-88-0
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.365
• Mol file: 134037-88-0.mol

Synonyms:(+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one

Chemical Property of (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one

There total 10 articles about (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one 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: 70.0%

((+)-2R,5S,7S)-7-phenylmethyl-7-carboxyl-2-phenyl-1-aza-3-oxa-bicyclo<3.3.0>octan-8-one (176243-48-4) → (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one (134037-88-0)

Guidance literature:

at 150 ℃; for 2h; under 0.5 Torr;

DOI:10.1016/0040-4020(96)00047-6

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one (134037-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / TsOH / toluene / Heating

2: LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 1 h

With toluene-4-sulfonic acid; lithium diisopropyl amide; In toluene;

DOI:10.1016/0040-4020(96)00047-6

Reference yield:

benzyl bromide (100-39-0) + (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → (+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one (134037-88-0) + (+)-(2R,5S,7S)-1-aza-3-oxa-2-phenyl-7-(phenylmethyl)bicyclo<3.3.0>octan-8-one (134107-62-3)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C;

DOI:10.1016/S0040-4039(00)79672-9

upstream raw materials:

benzyl bromide

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

((+)-2R,5S,7S)-7-phenylmethyl-7-carboxyl-2-phenyl-1-aza-3-oxa-bicyclo<3.3.0>octan-8-one

benzaldehyde

Downstream raw materials:

(-)-(2S,4R)-7-benzyl-2-hydroxymethyl-5-oxo-pyrrolidine