1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate

Base Information

• Chemical Name: 1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate
• CAS No.: 224645-86-7
• Molecular Formula: C₂₁H₂₆Cl₃NO₆
• Molecular Weight: 494.8
• NSC Number: 715407
• DSSTox Substance ID: DTXSID301106434
• ChEMBL ID: CHEMBL1977094
• Mol file: 224645-86-7.mol

Synonyms:NSC715407;CHEMBL1977094;DTXSID301106434;NSC-715407;NCI60_039848;1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate;224645-86-7

Chemical Property of 1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 493.082571
• Heavy Atom Count: 31
• Complexity: 640

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OCC(Cl)(Cl)Cl)CC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OCC(Cl)(Cl)Cl)CC(=O)OCC2=CC=CC=C2

Technology Process of 1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate

There total 9 articles about 1-(1,1-Dimethylethyl) 2-(2,2,2-trichloroethyl) (2S,4S)-4-[2-oxo-2-(phenylmethoxy)ethyl]-1,2-pyrrolidinedicarboxylate 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:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → (2S,4S)-4-Benzyloxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2,2,2-trichloro-ethyl) ester (224645-86-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: KHMDS; Et₃B / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: 63 percent / TFA; H₂O / tetrahydrofuran

3.1: LAH / tetrahydrofuran / Heating

4.1: CH₂Cl₂ / 0 °C

5.1: 88 percent

6.1: 85 percent / DIC; DMAP

7.1: O₃ / CH₂Cl₂; methanol

7.2: 90 percent / dimethyl sulfide

8.1: PDC / dimethylformamide

9.1: NaI; NaHCO₃ / dimethylformamide

With dmap; lithium aluminium tetrahydride; dipyridinium dichromate; triethyl borane; water; potassium hexamethylsilazane; sodium hydrogencarbonate; ozone; dacarbazine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Enolization / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Acylation / 5.1: Oxidation / 6.1: Esterification / 7.1: Oxidation / 7.2: Decomposition / 8.1: Oxidation / 9.1: Alkylation;

DOI:10.1016/S0040-4039(99)00345-7

Reference yield:

(+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-allylbicyclo<3.3.0>octan-8-one (138231-10-4) → (2S,4S)-4-Benzyloxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2,2,2-trichloro-ethyl) ester (224645-86-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 63 percent / TFA; H₂O / tetrahydrofuran

2.1: LAH / tetrahydrofuran / Heating

3.1: CH₂Cl₂ / 0 °C

4.1: 88 percent

5.1: 85 percent / DIC; DMAP

6.1: O₃ / CH₂Cl₂; methanol

6.2: 90 percent / dimethyl sulfide

7.1: PDC / dimethylformamide

8.1: NaI; NaHCO₃ / dimethylformamide

With dmap; lithium aluminium tetrahydride; dipyridinium dichromate; water; sodium hydrogencarbonate; ozone; dacarbazine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Hydrolysis / 2.1: Reduction / 3.1: Acylation / 4.1: Oxidation / 5.1: Esterification / 6.1: Oxidation / 6.2: Decomposition / 7.1: Oxidation / 8.1: Alkylation;

DOI:10.1016/S0040-4039(99)00345-7

Reference yield:

(3R,5S)-3-Allyl-5-hydroxymethyl-pyrrolidine → (2S,4S)-4-Benzyloxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2,2,2-trichloro-ethyl) ester (224645-86-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 0 °C

2.1: 88 percent

3.1: 85 percent / DIC; DMAP

4.1: O₃ / CH₂Cl₂; methanol

4.2: 90 percent / dimethyl sulfide

5.1: PDC / dimethylformamide

6.1: NaI; NaHCO₃ / dimethylformamide

With dmap; dipyridinium dichromate; sodium hydrogencarbonate; ozone; dacarbazine; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Oxidation / 3.1: Esterification / 4.1: Oxidation / 4.2: Decomposition / 5.1: Oxidation / 6.1: Alkylation;

DOI:10.1016/S0040-4039(99)00345-7

upstream raw materials:

benzyl bromide

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

(+)-(2R,5S,7R)-1-aza-3-oxa-2-phenyl-7-allylbicyclo<3.3.0>octan-8-one

(3R,5S)-3-allyl-5-hydroxymethyl-2-pyrrolidinone

Refernces