(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

Base Information

Chemical Name:(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol
CAS No.:791635-41-1
Molecular Formula:C₃₅H₅₃NO₂Si
Molecular Weight:547.897
Hs Code.:

Synonyms:(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

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Chemical Property of (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

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Technology Process of (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

There total 10 articles about (3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-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: 100.0%

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

: 791635-41-1
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h;
DOI:10.1021/ol048353g

Reference yield:

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

: 791635-41-1
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 3.89 g / t-BuLi / diethyl ether / 2 h / -78 °C

2: 71 percent / tetrahydrofuran; toluene / 3 h / -10 °C

3: 90 percent / K₂CO₃ / methanol; H₂O / 20 °C

4: 94 percent / m-CPBA / CH₂Cl₂ / 20 °C

5: 80 percent / DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 20 °C

6: 66 percent / NH₂NH₂; AcOH / methanol / 2 h / -10 °C

7: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

8: TFA / CH₂Cl₂ / 2 h / -10 - 20 °C

9: 100 percent / NaBH₄ / methanol / 2 h / 20 °C

With manganese(IV) oxide; sodium tetrahydroborate; pyridine-SO₃ complex; tert.-butyl lithium; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; hydrazine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 2: aza-Prins cyclization / 6: Wharton's rearrangement;
DOI:10.1021/ol048353g

Reference yield:

: [1-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-octadeca-9,11-dienyl]-carbamic acid tert-butyl ester

: 791635-41-1
(3S,5R,7aR,11aS)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexadecahydro-1H-pyrrolo[2,1-j]quinoline-7-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 71 percent / tetrahydrofuran; toluene / 3 h / -10 °C

2: 90 percent / K₂CO₃ / methanol; H₂O / 20 °C

3: 94 percent / m-CPBA / CH₂Cl₂ / 20 °C

4: 80 percent / DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 20 °C

5: 66 percent / NH₂NH₂; AcOH / methanol / 2 h / -10 °C

6: 90 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

7: TFA / CH₂Cl₂ / 2 h / -10 - 20 °C

8: 100 percent / NaBH₄ / methanol / 2 h / 20 °C

With manganese(IV) oxide; sodium tetrahydroborate; pyridine-SO₃ complex; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; hydrazine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: aza-Prins cyclization / 5: Wharton's rearrangement;
DOI:10.1021/ol048353g