(2S,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 148017-39-4
• Molecular Formula: C12H21NO4S
• Molecular Weight: 275.36400
• DSSTox Substance ID: DTXSID10445483
• Mol file: 148017-39-4.mol

Synonyms:148017-39-4;(2S,4R)-TERT-BUTYL 4-(ACETYLTHIO)-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE;tert-butyl (2S,4R)-4-acetylsulfanyl-2-(hydroxymethyl)pyrrolidine-1-carboxylate;(2S,4R)-4-Acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol;SCHEMBL7805560;DTXSID10445483;A3238

Chemical Property of (2S,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 388.5±35.0 °C(Predicted)
• PKA: 14.77±0.10(Predicted)
• PSA: 92.14000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 1.57430
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 275.11912932
• Heavy Atom Count: 18
• Complexity: 327

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SC1CC(N(C1)C(=O)OC(C)(C)C)CO
• Isomeric SMILES: CC(=O)S[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)CO

Technology Process of (2S,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 7 articles about (2S,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 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:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (2S,4R)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (148017-39-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / triethylamine / CH₂Cl₂ / 0.75 h / Ambient temperature

2: 66 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.67 h / 0 °C

3: 89 percent / aq. NaOH / methanol / 0.33 h

4: 1.) triethylamine, 2.) sodium borohydride / 1.) CH₂Cl₂, 20 min, 2.) THF, EtOH, room temperature, 75 min

5: dimethylformamide / 3.75 h / 65 °C

With sodium hydroxide; sodium tetrahydroborate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2S,4R)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (148017-39-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.67 h / 0 °C

2: 89 percent / aq. NaOH / methanol / 0.33 h

3: 1.) triethylamine, 2.) sodium borohydride / 1.) CH₂Cl₂, 20 min, 2.) THF, EtOH, room temperature, 75 min

4: dimethylformamide / 3.75 h / 65 °C

With sodium hydroxide; sodium tetrahydroborate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → (2S,4R)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (148017-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) triethylamine, 2.) sodium borohydride / 1.) CH₂Cl₂, 20 min, 2.) THF, EtOH, room temperature, 75 min

2: dimethylformamide / 3.75 h / 65 °C

With sodium tetrahydroborate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.49.478

upstream raw materials:

tert-butyl (2S,4S)-2-(hydroxymethyl)-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate

potassium thioacetate

(R)-4-hydroxy-L-proline ethyl ester

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

C₃₈H₅₀N₄O₁₀S₂

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