(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Base Information

Chemical Name:(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one
CAS No.:791635-36-4
Molecular Formula:C₃₅H₅₁NO₂Si
Molecular Weight:545.881
Hs Code.:

Synonyms:(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

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Chemical Property of (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

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Technology Process of (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

There total 13 articles about (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-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: 72.0%

: 791635-35-3
(2S,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 791635-36-4
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -10 ℃; for 2h;
DOI:10.1021/jo0501846

Reference yield:

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

: 791635-36-4
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: t-BuLi / diethyl ether / 1 h / -78 °C

1.2: 61 percent / tetrahydrofuran; diethyl ether / 2 h / -78 °C

2.1: 71 percent / tetrahydrofuran; toluene / 3 h / -10 °C

3.1: 90 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

4.1: 94 percent / m-CPBA / CH₂Cl₂ / -10 - 20 °C

5.1: 80 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / -10 - 20 °C

6.1: 66 percent / NH₂NH₂; AcOH / methanol / -10 - 20 °C

7.1: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

8.1: 72 percent / TFA / CH₂Cl₂ / 2 h / -10 °C

With manganese(IV) oxide; pyridine-SO₃ complex; tert.-butyl lithium; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; hydrazine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 2.1: Prins cyclization / 6.1: Wharton rearrangement;
DOI:10.1021/jo0501846

Reference yield:

: 791635-28-4
(2S,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-3-formyloxy-non-1-enyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 791635-36-4
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

2: 94 percent / m-CPBA / CH₂Cl₂ / -10 - 20 °C

3: 80 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / -10 - 20 °C

4: 66 percent / NH₂NH₂; AcOH / methanol / -10 - 20 °C

5: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

6: 72 percent / TFA / CH₂Cl₂ / 2 h / -10 °C

With manganese(IV) oxide; pyridine-SO₃ complex; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; hydrazine; In methanol; dichloromethane; water; dimethyl sulfoxide; 4: Wharton rearrangement;
DOI:10.1021/jo0501846