(4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 136024-61-8
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374

Synonyms:(4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester

There total 11 articles about (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl 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: 84.0%

tert-butyl (2S,4R)-4-(benzyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (109953-95-9) → (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester (136024-61-8)

Guidance literature:

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 10 - 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)80968-6

Reference yield: 69.0%

(4R)-benzyloxy-(2S)-(N-methoxy-N-methylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1232834-99-9) → (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester (136024-61-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jm100839w

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (4R)-benzyloxy-(2S)-formylpyrrolidine-1-carboxylic acid tert-butyl ester (136024-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH

2: 54 percent / NaBH₄

3: 54 percent / DMSO; (COCl)2

With sodium tetrahydroborate; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; 3: Swern oxidation;

DOI:10.1016/j.tetlet.2005.09.021

upstream raw materials:

tert-butyl (2S,4R)-4-(benzyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(R)-4-hydroxy-L-proline ethyl ester

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

1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4R)-4-Benzyloxy-2-diethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-benzyloxy-2-dimethoxymethyl-pyrrolidine

(4R,5R)-5-((2S,4R)-4-Benzyloxy-2-dimethoxymethyl-pyrrolidine-1-carbonyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

(4S,5S)-5-((2S,4R)-4-Benzyloxy-2-dimethoxymethyl-pyrrolidine-1-carbonyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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