(2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

Base Information

• Chemical Name: (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester
• CAS No.: 367259-54-9
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48

Synonyms:(2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

Chemical Property of (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

Chemical Property:

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Technology Process of (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

There total 3 articles about (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl 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:

1-[(3-bromopropoxy)methyl]-benzene (54314-84-0) → (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367259-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; NaI / dimethylformamide / 18 h / 20 °C

2: 5.15 g / benzene; methanol; hexane / 1 h / 20 °C

With sodium hydride; sodium iodide; In methanol; hexane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo011160b

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367259-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; NaI / dimethylformamide / 18 h / 20 °C

2: 5.15 g / benzene; methanol; hexane / 1 h / 20 °C

With sodium hydride; sodium iodide; In methanol; hexane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo011160b

Reference yield:

(2S,4R)-4-(3-Benzyloxy-propoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (367260-47-7) + diazomethyl-trimethyl-silane (18107-18-1) → (2S,4R)-4-[3-(phenylmethoxy)propoxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester (367259-54-9)

Guidance literature:

In methanol; hexane; benzene; at 20 ℃; for 1h;

DOI:10.1021/jo011160b

upstream raw materials:

(2S,4R)-4-(3-Benzyloxy-propoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

diazomethyl-trimethyl-silane

1-[(3-bromopropoxy)methyl]-benzene

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(3-hydroxyphenyl)acetyl]amino]-1-oxoethyl]-4-[3-(phenylmethoxy)propoxy]-2-pyrrolidinecarboxylate

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[3-(phenylmethoxy)propoxy]-2-pyrrolidinecarboxylate

methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(3-hydroxyphenyl)acetyl]amino]-1-oxoethyl]-4-(3-hydroxypropoxy)-2-pyrrolidinecarboxylate

12-cyclohexyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

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