(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Chemical Name:(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
CAS No.:117811-74-2
Molecular Formula:C₁₆H₂₀N₂O₁₀S
Molecular Weight:432.408
Hs Code.:

Synonyms:(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of (2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

There total 9 articles about (2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-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: 75.0%

: 124-63-0
methanesulfonyl chloride

: 117811-73-1
(2S,4R)-2-Carboxymethoxymethyl-4-hydroxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 117811-74-2
(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 5 ℃; for 1h;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

: 101803-29-6
(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

: 117811-74-2
(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

3: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

4: aq. NaOH / tetrahydrofuran / 2 h

5: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

6: aq. 6N HCl / 3 h / Heating

7: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

8: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

: 104795-10-0
(2S,4R)-4-tert-butyldimethylsiloxy-2-hydroxymethyl-N-(4-nitrobenzyloxycarbonyl) pyrrolidine

: 117811-74-2
(2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

2: aq. NaOH / tetrahydrofuran / 2 h

3: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

4: aq. 6N HCl / 3 h / Heating

5: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

6: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

With hydrogenchloride; sodium hydroxide; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/S0968-0896(97)00142-9