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

Base Information

• Chemical Name: (2S,4R)-1-benzyloxycarbonyl-2-formyl-4-methoxycarbonyl-4-methylpyrrolidine
• CAS No.: 175793-14-3
• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.331
• Mol file: 175793-14-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2S,4R)-1-benzyloxycarbonyl-2-formyl-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: 75.0%

(2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methoxycarbonyl-4-methylpyrrolidine (175793-13-2) → (2S,4R)-1-benzyloxycarbonyl-2-formyl-4-methoxycarbonyl-4-methylpyrrolidine (175793-14-3)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane;

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

Reference yield:

(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-benzyloxycarbonyl-2-formyl-4-methoxycarbonyl-4-methylpyrrolidine (175793-14-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / NaBH₃CN, 2M HCl / tetrahydrofuran

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

3: 97 percent / Et₃N / CH₂Cl₂

4: TFA

5: DCCI / tetrahydrofuran

6: NaBH₄ / tetrahydrofuran

7: 75 percent / TPAP, NMO, 4 Angstroem sieves / CH₂Cl₂

With hydrogenchloride; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; sodium cyanoborohydride; 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:

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

benzyl chloroformate

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

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

Downstream raw materials:

(2S,4R)-1-benzyloxycarbonyl-2-(2-ethoxycarbonyl-(E)-ethenyl)-4-methoxycarbonyl-4-methylpyrrolidine