[(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

Base Information

• Chemical Name: [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester
• CAS No.: 909784-70-9
• Molecular Formula: C₂₉H₂₇F₆NO₃
• Molecular Weight: 551.529
• Mol file: 909784-70-9.mol

Synonyms:[(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

Chemical Property of [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

There total 14 articles about [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester 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:

1-((1R,2R,3S)-3-Isocyanato-2-phenyl-cyclopentyloxymethyl)-3,5-bis-trifluoromethyl-benzene + (S)-1-phenylethanol (1445-91-6) → [(1R,2S,3S)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester (909784-71-0) + [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester (909784-70-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In toluene; at 85 ℃;

DOI:10.1016/j.bmcl.2006.06.035

Reference yield:

(1S,2S)-3-Oxo-2-phenyl-cyclopentanecarboxylic acid methyl ester → [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester (909784-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / methanol

2: 62 percent / NaH / dimethylformamide

3: oxalyl chloride; DMF / CH₂Cl₂

4: NaN₃ / acetone; H₂O / -10 °C

5: toluene / 85 °C

6: DIPEA; DMAP / toluene / 85 °C

With dmap; sodium tetrahydroborate; sodium azide; oxalyl dichloride; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 5: Curtius rearrangement;

DOI:10.1016/j.bmcl.2006.06.035

Reference yield:

(1S,2S,3R)-3-Hydroxy-2-phenyl-cyclopentanecarboxylic acid methyl ester → [(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester (909784-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / NaH / dimethylformamide

2: oxalyl chloride; DMF / CH₂Cl₂

3: NaN₃ / acetone; H₂O / -10 °C

4: toluene / 85 °C

5: DIPEA; DMAP / toluene / 85 °C

With dmap; sodium azide; oxalyl dichloride; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 4: Curtius rearrangement;

DOI:10.1016/j.bmcl.2006.06.035

upstream raw materials:

(S)-1-phenylethanol

4-oxo-5-phenyl-cyclopentane-1,3-dicarboxylic acid dimethyl ester

ethyl 2,3-dicyano-3-phenylpropanoate

trans-(+/-)-2-Phenylcyclopentan-3-one-1-carboxylic acid

Downstream raw materials:

(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine