(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

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Chemical Name:(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one
CAS No.:914389-46-1
Molecular Formula:C₂₅H₃₃N₃O₆
Molecular Weight:471.554
Hs Code.:

Synonyms:(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

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Chemical Property of (4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

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Technology Process of (4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

There total 7 articles about (4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one 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: 52.0%

: 914389-45-0
(4R)-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

: 5437-45-6
Benzyl bromoacetate

: 914389-46-1
(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

Guidance literature:: With caesium carbonate; In acetonitrile; at 20 ℃; for 4h;
DOI:10.1021/jo061189l

Reference yield:

: 2-oxomethylene-pyrrolidine-1-carboxylic acid benzyl ester

: 914389-46-1
(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 12 h / -40 - 20 °C

2.1: 98 percent / H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

3.1: L-Boc-Phe-OH / ethyl acetate; hexane

3.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

4.1: 50 percent / HOBt; DCC / tetrahydrofuran / 48 h / 20 °C

5.1: 65 percent / aq. CAN / acetonitrile / 0 °C

6.1: 52 percent / Cs₂CO₃ / acetonitrile / 4 h / 20 °C

With ammonium cerium(IV) nitrate; N-tert-butoxycarbonyl-L-phenylalanine; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo061189l

Reference yield:

: 914389-32-5
(+/-)-5-benzyloxycarbonyl-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one

: 914389-46-1
(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

2.1: L-Boc-Phe-OH / ethyl acetate; hexane

2.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

3.1: 50 percent / HOBt; DCC / tetrahydrofuran / 48 h / 20 °C

4.1: 65 percent / aq. CAN / acetonitrile / 0 °C

5.1: 52 percent / Cs₂CO₃ / acetonitrile / 4 h / 20 °C

With ammonium cerium(IV) nitrate; N-tert-butoxycarbonyl-L-phenylalanine; hydrogen; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; acetonitrile;
DOI:10.1021/jo061189l