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

Base Information

Chemical Name:[(1R,2S,3S)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester
CAS No.:909784-71-0
Molecular Formula:C₂₉H₂₇F₆NO₃
Molecular Weight:551.529
Hs Code.:

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

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

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

There total 13 articles about [(1R,2S,3S)-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

: 1445-91-6
(S)-1-phenylethanol

: 909784-71-0
[(1R,2S,3S)-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-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

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

: 909784-71-0
[(1R,2S,3S)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

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:

: 859317-18-3
4-oxo-5-phenyl-cyclopentane-1,3-dicarboxylic acid dimethyl ester

: 909784-71-0
[(1R,2S,3S)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentyl]-carbamic acid (S)-1-phenyl-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: aq. HCl / 48 h / Heating

2: HCl; HC(OMe)3 / 16 h / 65 °C

3: NaBH₄ / methanol

4: 62 percent / NaH / dimethylformamide

5: oxalyl chloride; DMF / CH₂Cl₂

6: NaN₃ / acetone; H₂O / -10 °C

7: toluene / 85 °C

8: DIPEA; DMAP / toluene / 85 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; sodium azide; oxalyl dichloride; sodium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trimethyl orthoformate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 7: Curtius rearrangement;
DOI:10.1016/j.bmcl.2006.06.035