(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

Base Information

Chemical Name:(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one
CAS No.:494836-45-2
Molecular Formula:C₁₉H₃₀N₄O₃
Molecular Weight:362.472
Hs Code.:

Synonyms:(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

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Chemical Property of (1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

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Technology Process of (1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

There total 11 articles about (1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one 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: 75.0%

: 494836-34-9
(1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

: 494836-45-2
(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: With pyridine hydrogenfluoride; In acetonitrile;
DOI:10.1016/S0960-894X(02)00612-1

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 494836-45-2
(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: LiHMDS / tetrahydrofuran / -78 °C

1.2: 92 percent / tetrahydrofuran / -78 °C

2.1: Dibal-H / toluene / -78 °C

3.1: Et₃N; DMAP / CH₂Cl₂

4.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

5.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 760 Torr

6.1: LiHMDS / tetrahydrofuran / -78 °C

6.2: 74 percent / tetrahydrofuran / -78 °C

7.1: t-BuLi / tetrahydrofuran / -78 °C

7.2: 72 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

8.1: B-bromocatecholborane / CH₂Cl₂

9.1: toluene / Heating

10.1: 94 percent / KH / tetrahydrofuran

11.1: 75 percent / HF*pyr / acetonitrile

With dmap; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/S0960-894X(02)00612-1

Reference yield:

: 494836-25-8
5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 494836-45-2
(1R,3S,6R,8S,8aS)-6-Azido-6-cyclohex-1-enylmethyl-1-ethyl-3-hydroxymethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: Dibal-H / toluene / -78 °C

2.1: Et₃N; DMAP / CH₂Cl₂

3.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

4.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 760 Torr

5.1: LiHMDS / tetrahydrofuran / -78 °C

5.2: 74 percent / tetrahydrofuran / -78 °C

6.1: t-BuLi / tetrahydrofuran / -78 °C

6.2: 72 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

7.1: B-bromocatecholborane / CH₂Cl₂

8.1: toluene / Heating

9.1: 94 percent / KH / tetrahydrofuran

10.1: 75 percent / HF*pyr / acetonitrile

With dmap; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/S0960-894X(02)00612-1