(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

Base Information

Chemical Name:(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane
CAS No.:857685-72-4
Molecular Formula:C₂₃H₃₂F₃NO₃
Molecular Weight:427.507
Hs Code.:

Synonyms:(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

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Chemical Property of (1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

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Technology Process of (1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

There total 19 articles about (1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane 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: 88.0%

: 857685-71-3
(1R,5S,7R)-7-(2-((tert-butyl)dimethylsilanyloxy)ethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

: 857685-72-4
(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1021/jo047882v

Reference yield:

: 857685-61-1
(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone oxime

: 857685-72-4
(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 11 steps

1.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

2.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

3.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

4.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

6.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

6.2: tetrahydrofuran; pentane / 3 h / -78 °C

7.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

8.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

9.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

10.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

11.1: HF*pyridine complex / tetrahydrofuran / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium borohydride; hydrogen; iodine; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; urea; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; acetonitrile; tert-butyl alcohol; pentane; 2.1: Michael addition;
DOI:10.1016/j.tet.2007.03.031

Reference yield:

: 857685-64-4
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-(3-hydroxypropyl)-2-nitro-cyclopentane

: 857685-72-4
(1R,5S,7R)-7-(2-hydroxyethyl)-1-((1R)-2-benzyloxy-1-methylethyl)-6-trifluoroacetyl-6-azaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

3.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / 3 h / -78 °C

4.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

5.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

6.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

7.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

8.1: HF*pyridine complex / tetrahydrofuran / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; hydrogen; iodine; tert.-butyl lithium; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; pentane;
DOI:10.1016/j.tet.2007.03.031