(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

Base Information

Chemical Name:(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine
CAS No.:457614-04-9
Molecular Formula:C₂₀H₃₀N₂O₃
Molecular Weight:346.47
Hs Code.:

Synonyms:(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

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Chemical Property of (1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

Chemical Property:

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Technology Process of (1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

There total 11 articles about (1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine 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:

: 457614-07-2
(2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane

: 457614-04-9
(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

Guidance literature:: (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane; With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; under 760 Torr;

In methanol; for 4h; Heating;
DOI:10.1055/s-2002-28505

Reference yield:

: 144090-56-2
2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal

: 457614-04-9
(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C

1.2: chiral cyclopentadienyl titanium complex / tetrahydrofuran; cyclohexane; diethyl ether / 3 h / -78 °C

1.3: 69 percent / tetrahydrofuran; cyclohexane; diethyl ether / 4 h / -78 °C

2.1: 87 percent / imidazole / CH₂Cl₂ / 20 °C

3.1: BH₃ / tetrahydrofuran / 4 h / 0 - 20 °C

3.2: aq. H₂O₂; NaOH / 2 h / 20 °C

3.3: 1.56 g / TBAF / tetrahydrofuran / 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: DPPA; PPh₃; DIAD / 12 h / 0 - 20 °C

6.1: 95 mg / aq. CAN / acetonitrile / 0.17 h / 0 °C

7.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

7.2: 90 percent / tetrahydrofuran / 48 h / 20 °C

8.1: TBAF / tetrahydrofuran / 4 h / 20 °C

9.1: 295 mg / aq. AcOH / tetrahydrofuran / 12 h / 55 - 60 °C

10.1: DMAP; pyridine / 2 h / 0 °C

11.1: H₂; Et₃N / 10 percent Pd/C / methanol / 20 °C / 760 Torr

11.2: 104 mg / methanol / 4 h / Heating

With pyridine; 1H-imidazole; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; sodium hydride; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1055/s-2002-28505

Reference yield:

: 457613-95-5
(3R,4S)-1-[(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-4-(4-methoxyphenoxy)hex-5-en-3-ol

: 457614-04-9
(1S,6S,8aS)-6-[(tert-butoxycarbonyl)amino]-1-benzyloxyoctahydroindolizidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 87 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: BH₃ / tetrahydrofuran / 4 h / 0 - 20 °C

2.2: aq. H₂O₂; NaOH / 2 h / 20 °C

2.3: 1.56 g / TBAF / tetrahydrofuran / 20 °C

3.1: 94 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: DPPA; PPh₃; DIAD / 12 h / 0 - 20 °C

5.1: 95 mg / aq. CAN / acetonitrile / 0.17 h / 0 °C

6.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

6.2: 90 percent / tetrahydrofuran / 48 h / 20 °C

7.1: TBAF / tetrahydrofuran / 4 h / 20 °C

8.1: 295 mg / aq. AcOH / tetrahydrofuran / 12 h / 55 - 60 °C

9.1: DMAP; pyridine / 2 h / 0 °C

10.1: H₂; Et₃N / 10 percent Pd/C / methanol / 20 °C / 760 Torr

10.2: 104 mg / methanol / 4 h / Heating

With pyridine; 1H-imidazole; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; diphenyl-phosphinic acid; borane; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1055/s-2002-28505