1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate
• CAS No.: 932040-48-7
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• Mol file: 932040-48-7.mol

Synonyms:1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property of 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property:

• Boiling Point: 350.2±42.0 °C(Predicted)
• Density: 1.189±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate

There total 1 articles about 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate 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:

ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate (932040-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / toluene / 20 °C

2: lithium triethylborohydride / toluene / 0.5 h / -50 - -45 °C

With dmap; lithium triethylborohydride; In toluene;

Reference yield:

1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate (932040-48-7) → (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564265-94-6,1564265-93-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

2.1: water; lithium hydroxide / ethanol

3.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran

4.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

5.1: isopropyl alcohol / 60 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h

7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C

7.2: 18 h / 20 °C

8.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C

With pyridine; hydrogenchloride; dmap; ammonia; water; diethylzinc; benzotriazol-1-ol; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; isopropyl alcohol; acetonitrile; 4.1: |Simmons-Smith Cyclopropanation;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate (932040-48-7) → (R)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564265-95-7,1564265-93-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

2.1: water; lithium hydroxide / ethanol

3.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran

4.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

5.1: isopropyl alcohol / 60 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h

7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C

7.2: 18 h / 20 °C

8.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C

With pyridine; hydrogenchloride; dmap; ammonia; water; diethylzinc; benzotriazol-1-ol; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; isopropyl alcohol; acetonitrile; 4.1: |Simmons-Smith Cyclopropanation;

DOI:10.1016/j.bmc.2013.12.061

upstream raw materials:

ethyl (R)-2-pyrrolidone-5-carboxylate

Downstream raw materials:

(S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

(R)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

(R)-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinenitrile