(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

Base Information

Chemical Name:(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one
CAS No.:183813-71-0
Molecular Formula:C₂₁H₃₈N₂O₂Si
Molecular Weight:378.63
Hs Code.:

Synonyms:(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

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Chemical Property of (3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

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Technology Process of (3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

There total 7 articles about (3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-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: 39.0%

: (S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-6-hydroxy-2,3,8,8a-tetrahydro-1H-indolizin-5-one

: 183593-46-6
(3S,8aS)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

: 183813-71-0
(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

Guidance literature:: With ammonia; In methanol; for 72h; Ambient temperature;
DOI:10.1021/ja961887v

Reference yield:

: 183593-62-6
1-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone

: 183813-71-0
(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, overnight

2: 74 percent / tetraethylammonium tosylate / carbon rod anode, Pt cathode

3: 94 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

4: 94 percent / H₂, MeONa / 5percent Pd/C

5: 95 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) LDA, 2.) O₂ / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

7: 39 percent / NH₃ / methanol / 72 h / Ambient temperature

With ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; sodium hydride; tetraethylammonium tosylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/ja961887v

Reference yield:

: (S)-7-(1-Chloro-cyclohexyl)-3-hydroxymethyl-hexahydro-indolizin-5-one

: 183813-71-0
(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / H₂, MeONa / 5percent Pd/C

2: 95 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 1.) LDA, 2.) O₂ / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

4: 39 percent / NH₃ / methanol / 72 h / Ambient temperature

With ammonia; hydrogen; oxygen; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/ja961887v