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ChemicalBook CAS DataBase List (S,S,R,S)-Orlistat
130193-42-9

(S,S,R,S)-Orlistat synthesis

5synthesis methods
Tetradecanal, 3-[(4-methoxyphenyl)methoxy]-, (3S)-

1369787-81-4
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Yield:-

Steps:

Multi-step reaction with 9 steps
1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -5 °C
1.2: -78 - 0 °C
1.3: 1 h / 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -10 °C
2.2: 0.33 h / -10 °C
3.1: methanol / 1 h
4.1: lithium hydroxide / tetrahydrofuran; methanol; water / 20 °C
5.1: benzenesulfonyl chloride / pyridine / 20 °C
6.1: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.33 h / 20 °C
7.2: 2 h / 20 °C
8.1: trifluoroacetic acid / dichloromethane / 1 h / 10 °C
9.1: tetrahydrofuran / 0.33 h / 20 °C

References:

Aubry, Sylvain;Aubert, Genevieve;Cresteil, Thierry;Crich, David [Organic and Biomolecular Chemistry,2012,vol. 10,# 13,p. 2629 - 2632]

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