(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

Base Information

Chemical Name:(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol
CAS No.:361520-02-7
Molecular Formula:C₂₇H₃₉Cl₃N₂O₅
Molecular Weight:577.976
Hs Code.:

Synonyms:(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

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Chemical Property of (3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

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Technology Process of (3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

There total 16 articles about (3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol 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: 62.0%

: 361520-01-6
(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 361520-02-7
(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1021/ja016030z

Reference yield:

: 361520-05-0
(S)-2-[(methoxycarbonyl)amino]-3-(4-methoxyphenyl) propan-1-ol

: 361520-02-7
(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / aq. KOH / 50 °C

2: 73 percent / triphenylphosphine; NEt₃; pyridine / CCl₄; acetonitrile / 24 h / 27 - 30 °C

3: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C

4: 0.48 g / pyridine; DMAP / 20 °C

5: 96 percent / H₂; PtO₂ / ethyl acetate / 20 °C / 760.05 Torr

6: 79 percent / K₂CO₃ / methanol

7: 97 percent / K₂CO₃ / acetone; dimethylformamide

8: 87 percent / BBr₃ / CH₂Cl₂ / 1 h / -60 - 0 °C

9: 98 percent / Cs₂CO₃ / acetone / 2 h / 50 °C

10: LiAlH₄ / tetrahydrofuran / 48 h / Heating

11: 62 percent / NaHCO₃ / tetrahydrofuran; H₂O / 20 °C

With pyridine; dmap; platinum(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja016030z

Reference yield:

: 4703-32-6
(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid

: 361520-02-7
(3S,1S')-1-{2'-hydroxy-1'-[4-(3-methyl-but-2-enyloxy)benzyl]-ethyl}-3-[N-2,2,2-trichloroethoxycarbonyl-N-methyl-amino]-1-azaspiro[4.5]decane-8-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 73 percent / triphenylphosphine; NEt₃; pyridine / CCl₄; acetonitrile / 24 h / 27 - 30 °C

2: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C

3: 0.48 g / pyridine; DMAP / 20 °C

4: 96 percent / H₂; PtO₂ / ethyl acetate / 20 °C / 760.05 Torr

5: 79 percent / K₂CO₃ / methanol

6: 97 percent / K₂CO₃ / acetone; dimethylformamide

7: 87 percent / BBr₃ / CH₂Cl₂ / 1 h / -60 - 0 °C

8: 98 percent / Cs₂CO₃ / acetone / 2 h / 50 °C

9: LiAlH₄ / tetrahydrofuran / 48 h / Heating

10: 62 percent / NaHCO₃ / tetrahydrofuran; H₂O / 20 °C

With pyridine; dmap; platinum(IV) oxide; lithium aluminium tetrahydride; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja016030z