(2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine
• CAS No.: 175792-86-6
• Molecular Formula: C₂₇H₃₆N₂O₄
• Molecular Weight: 452.594
• Mol file: 175792-86-6.mol

Synonyms:(2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine

Chemical Property of (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine

There total 1 articles about (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine 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: 73.0%

(3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175792-75-3) → (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine (175792-86-6)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00114-1

Reference yield:

(2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine (175792-86-6) → (2S,4R)-4-Methyl-pyrrolidine-1,2,4-tricarboxylic acid 1-benzyl ester 2-(2,5-dioxo-pyrrolidin-1-yl) ester 4-methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / H₂, TFA / Pd(OH)2/C / methanol / 3102.9 Torr

2: 97 percent / Et₃N / CH₂Cl₂

3: TFA

4: DCCI / tetrahydrofuran

With hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0040-4039(96)00114-1

Reference yield:

(2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine (175792-86-6) → (2S,4R)-1-benzyloxycarbonyl-2-formyl-4-methoxycarbonyl-4-methylpyrrolidine (175793-14-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / H₂, TFA / Pd(OH)2/C / methanol / 3102.9 Torr

2: 97 percent / Et₃N / CH₂Cl₂

3: TFA

4: DCCI / tetrahydrofuran

5: NaBH₄ / tetrahydrofuran

6: 75 percent / TPAP, NMO, 4 Angstroem sieves / CH₂Cl₂

With sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0040-4039(96)00114-1

upstream raw materials:

(3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole

Downstream raw materials:

(2S,4R)-1-benzyloxycarbonyl-2-formyl-4-methoxycarbonyl-4-methylpyrrolidine

(2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methoxycarbonyl-4-methylpyrrolidine

(2S,4R)-1-benzyloxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine-2-carboxylic acid

(2S,4R)-1-benzyloxycarbonyl-2-tert-butoxycarbonyl-4-methoxycarbonyl-4-methylpyrrolidine