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

Base Information

• Chemical Name: (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine
• CAS No.: 909784-57-2
• Molecular Formula: C₂₀H₁₉F₆NO
• Molecular Weight: 403.367
• Mol file: 909784-57-2.mol

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

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

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-cyclopentylamine

There total 15 articles about (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine 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:

[(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester (909784-70-9) → (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine (909784-57-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 2585.74 Torr;

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-cyclopentylamine (909784-57-2)

Guidance literature:

Multi-step reaction with 7 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

7: H₂ / Pd/C / ethanol / 2585.74 Torr

With dmap; sodium tetrahydroborate; sodium azide; oxalyl dichloride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; ethanol; 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-cyclopentylamine (909784-57-2)

Guidance literature:

Multi-step reaction with 6 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

6: H₂ / Pd/C / ethanol / 2585.74 Torr

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

DOI:10.1016/j.bmcl.2006.06.035

upstream raw materials:

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

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