tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

Base Information

Chemical Name:tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate
CAS No.:852052-42-7
Molecular Formula:C₂₆H₃₅NO₃
Molecular Weight:409.569
Hs Code.:

Synonyms:tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

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Chemical Property of tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

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Technology Process of tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

There total 2 articles about tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate 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: 31.0%

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 119619-67-9
(E)-7-oxo-hept-2-enoic acid tert-butyl ester

: 852052-41-6
tert-butyl (3S,αS)-3-(N-benzyl-N-(α-methylbenzyl)amino)-7-oxoheptanoate

: 852052-42-7
tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

(E)-7-oxo-hept-2-enoic acid tert-butyl ester; In tetrahydrofuran; at -78 - -20 ℃; for 4h;
DOI:10.1039/b500223k

Reference yield:

: 117471-84-8
1,1-dimethylethyl (E)-7-hydroxyhept-2-enoate

: 852052-42-7
tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 56 percent / PCC; NaOAc / CH₂Cl₂ / 2 h / 0 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: 31 percent / tetrahydrofuran / 4 h / -78 - -20 °C

With n-butyllithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b500223k

Reference yield:

: 852052-42-7
tert-butyl (1R,2S,6S,αS)-2-hydroxy-6-N-benzyl-N-(α-methylbenzylamino)cyclohexanoate

: (1R,2S,6S)-2-hydroxy-6-aminocyclohexanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / H₂ / Pd(OH)2/C / methanol / 16 h / 3800 Torr

2: 73 percent / TFA / CH₂Cl₂ / 16 h / 20 °C

With hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane;
DOI:10.1039/b500223k