(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

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Chemical Name:(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione
CAS No.:566905-11-1
Molecular Formula:C₂₈H₃₄N₂O₆S
Molecular Weight:526.654
Hs Code.:

Synonyms:(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

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Chemical Property of (3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

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Technology Process of (3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

There total 1 articles about (3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione 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: 90.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 566905-10-0
(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-7-(phenylsulfonyl)-2,7-diazaspiro[4.5]decane-1,10-dione

: 566905-11-1
(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja034464j

Reference yield:

: 566905-11-1
(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

: 566905-17-7
tert-butyl (2S,3aS,7aS,10bS)-9-[3-(acetyloxy)propyl]-2-2-(hydroxyethyl)-5-(phenylsulfonyl)-2,3,4,5,6,7,7a,10b-octahydro-1H-furo[3,2:3,4]pyrrolo[3,2:1,5]cyclopenta[1,2-c]pyridine-1-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 13 h / 20 °C

2.1: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

3.1: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

4.1: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

5.1: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

7.1: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

8.1: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

9.1: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

10.1: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 - 20 °C

11.1: 7.57 g / pyridine / 12 h / 20 °C

12.1: 37 percent / p-TsOH monohydrate / CH₂Cl₂ / 1.2 h / 20 °C

With dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; lithium borohydride; ethanol; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j

Reference yield:

: 566905-11-1
(3S,5R)-2-benzyl-7-(phenylsulfonyl)-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2,7-diaza-spiro[4.5]decane-1,10-dione

: 3-[(6aS,7aS,11aS,14bS)-1-oxo-9-(phenylsulfonyl)-1,2,3,4,6a,7,8,9,10,11,11a,14b-dodecahydrofuro[2,3:3,4]pyrido[3,4:1,5]cyclopenta[1,2:4,5]pyrrolo[1,2-a]azocin-13-yl]propyl acetate

Guidance literature:: Multi-step reaction with 17 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 13 h / 20 °C

2.1: 95 percent / K₃PO₄; PdCl₂(dppf) / dimethylformamide / 3 h / 80 °C

3.1: 92 percent / Pd/C / methanol / 1.5 h / 20 °C

4.1: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C

5.1: 96 percent / CSA / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 19 h / 3 - 20 °C

7.1: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

8.1: 5.71 g / aq. NaHCO₃ / ethyl acetate / 1 h / 20 °C

9.1: 68 percent / DMAP; Et₃N / tetrahydrofuran / 11 h / 20 °C

10.1: DIBAL-H / toluene; CH₂Cl₂ / 2 h / -78 - 20 °C

11.1: 7.57 g / pyridine / 12 h / 20 °C

12.1: 37 percent / p-TsOH monohydrate / CH₂Cl₂ / 1.2 h / 20 °C

13.1: tri-n-butylphosphine / tetrahydrofuran / 16 h / 20 °C

14.1: 3.09 g / aq. K₂HPO₄; mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

15.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 1.76 g / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide*HCl / tetrahydrofuran / 3 h / 20 °C

17.1: 86 percent / Ru[(PCy₂)(=CH-Ph)(N,N'-Mes₂-imidazolidin-2-yl)]Cl₂ / CH₂Cl₂ / 2 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; dipotassium hydrogenphosphate; lithium borohydride; ethanol; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j