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

Base Information

• Chemical Name: (2R,3S,5R_.6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
• CAS No.: 339160-98-4
• Molecular Formula: C₃₂H₃₄N₂O₃
• Molecular Weight: 494.634

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

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

Chemical Property:

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

There total 4 articles about (2R,3S,5R_.6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl 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: 93.0%

trimethylsilyl cyanide (7677-24-9) + (3S,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-96-2) → (2R,3S,5R.6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-98-4)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃; for 0.5h;

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)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-98-4)

Guidance literature:

Multi-step reaction with 4 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

With dmap; 18-crown-6 ether; carbon dioxide; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 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)-2-cyano-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-98-4)

Guidance literature:

Multi-step reaction with 3 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

With dmap; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja0042332

upstream raw materials:

trimethylsilyl cyanide

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

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

Downstream raw materials:

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

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

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

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