methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate
• CAS No.: 1451055-29-0
• Molecular Formula: C₂₄H₃₀N₂O₄
• Molecular Weight: 410.513
• Mol file: 1451055-29-0.mol

Synonyms:methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

Chemical Property of methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

There total 6 articles about methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate 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:

methyl (2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylate (1451054-70-8) + 1-hydroxy-2-naphthoic acid (86-48-6) → methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate (1451055-29-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

Reference yield:

(2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester (1451054-80-0) → methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate (1451055-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; water / tetrahydrofuran / 6 h / 75 °C

2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → methyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate (1451055-29-0)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / dichloromethane / 16 h / 0 °C / Reflux

2: sodium azide / N,N-dimethyl-formamide / 16 h / 60 °C

3: dichloromethane / 16 h / 20 °C

4: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C

5: triphenylphosphine; water / tetrahydrofuran / 6 h / 75 °C

6: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With pyridine; sodium azide; water; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(2S,4S)-4-azido-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

methyl (2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylate

1-hydroxy-2-naphthoic acid

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

ethyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

(2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid

tert-butyl (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylate

(2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid amide