(2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid

Base Information

• Chemical Name: (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid
• CAS No.: 339161-02-3
• Molecular Formula: C₂₄H₂₉NO₃
• Molecular Weight: 379.499
• Mol file: 339161-02-3.mol

Synonyms:(2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid

Chemical Property of (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid

There total 6 articles about (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid 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: 88.0%

(2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carbonitrile (339161-00-1) → (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid (339161-02-3)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 150 ℃; for 40h;

DOI:10.1021/ja0042332

Reference yield:

(3R,5R,6S)-3-Cyclohexylmethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester → (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid (339161-02-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / KN(SiMe₃)2; 18-crown-6; CO₂ / tetrahydrofuran; toluene

2: DIBAL-H / CH₂Cl₂; toluene / 0.67 h / -78 °C

3: 0.168 g / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

4: 93 percent / BF₃*Et₂O / acetonitrile / 0.5 h / -20 °C

5: 95 percent / H₂ / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr

6: 88 percent / KOH / ethane-1,2-diol / 40 h / 150 °C

With dmap; potassium hydroxide; 18-crown-6 ether; carbon dioxide; boron trifluoride diethyl etherate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethylene glycol; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/ja0042332

Reference yield:

(3S,5R,6S)-3-cyclohexylmethyl-2-oxo-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester (339160-94-0) → (2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carboxylic acid (339161-02-3)

Guidance literature:

Multi-step reaction with 5 steps

1: DIBAL-H / CH₂Cl₂; toluene / 0.67 h / -78 °C

2: 0.168 g / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

3: 93 percent / BF₃*Et₂O / acetonitrile / 0.5 h / -20 °C

4: 95 percent / H₂ / Pd/C / ethyl acetate / 12 h / 20 °C / 760.05 Torr

5: 88 percent / KOH / ethane-1,2-diol / 40 h / 150 °C

With dmap; potassium hydroxide; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In dichloromethane; ethylene glycol; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/ja0042332

upstream raw materials:

(2R,3S,5R,6S)-3-cyclohexylmethyl-5,6-diphenyl-morpholine-2-carbonitrile

(3S,5R,6S)-3-cyclohexylmethyl-2-oxo-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester

(2R,3S,5R_.6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(3S,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Downstream raw materials:

(2R,3S)-nor-C-statine hydrochloride