1-Pyrrolidinecarboxylic acid, 4-(dimethylamino)-2-[[4-(methoxycarbonyl)phenoxy]methyl]-, 1,1-dimethylethyl ester, (2S,4S)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 4-(dimethylamino)-2-[[4-(methoxycarbonyl)phenoxy]methyl]-, 1,1-dimethylethyl ester, (2S,4S)-
CAS No.:316123-29-2
Molecular Formula:C20H30N2O5
Molecular Weight:378.469
Hs Code.:
Mol file:316123-29-2.mol

Synonyms:

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 4-(dimethylamino)-2-[[4-(methoxycarbonyl)phenoxy]methyl]-, 1,1-dimethylethyl ester, (2S,4S)-

Chemical Property:

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Technology Process of 1-Pyrrolidinecarboxylic acid, 4-(dimethylamino)-2-[[4-(methoxycarbonyl)phenoxy]methyl]-, 1,1-dimethylethyl ester, (2S,4S)-

There total 6 articles about 1-Pyrrolidinecarboxylic acid, 4-(dimethylamino)-2-[[4-(methoxycarbonyl)phenoxy]methyl]-, 1,1-dimethylethyl ester, (2S,4S)- 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:

: (2S,4R)-4-Acetoxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 316123-29-2
methyl 4-[1-tert-butoxycarbonyl-(4S)-dimethylamino-(2S)-pyrrolidinyl]methoxybenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 39 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 14 h / Heating

2.1: 96 percent / K₂CO₃ / methanol / 1 h / 20 °C

3.1: DIPEA / CH₂Cl₂ / 0.5 h / -78 °C

3.2: CH₂Cl₂ / 0.5 h / -78 °C

4.1: tetrahydrofuran / 18.3 h / -78 - 5 °C

With di-isopropyl azodicarboxylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Mitsunobu reaction;
DOI:10.1248/cpb.54.1515

Reference yield:

: 316122-23-3
methyl 4-[1-tert-butoxycarbonyl-(4R)-hydroxy-(2S)-pyrrolidinyl]methoxybenzoate

: 316123-29-2
methyl 4-[1-tert-butoxycarbonyl-(4S)-dimethylamino-(2S)-pyrrolidinyl]methoxybenzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIPEA / CH₂Cl₂ / 0.5 h / -78 °C

1.2: CH₂Cl₂ / 0.5 h / -78 °C

2.1: tetrahydrofuran / 18.3 h / -78 - 5 °C

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.54.1515

Reference yield:

: 316122-37-9
methyl 4-[N-tert-butoxycarbonyl-(4R)-acetoxy-(2S)-pyrrolidinylmethoxy]benzoate

: 316123-29-2
methyl 4-[1-tert-butoxycarbonyl-(4S)-dimethylamino-(2S)-pyrrolidinyl]methoxybenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / K₂CO₃ / methanol / 1 h / 20 °C

2.1: DIPEA / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.5 h / -78 °C

3.1: tetrahydrofuran / 18.3 h / -78 - 5 °C

With potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.54.1515