(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

Base Information

Chemical Name:(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one
CAS No.:184583-22-0
Molecular Formula:C₂₁H₂₀N₄O₃
Molecular Weight:376.415
Hs Code.:

Synonyms:(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

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Chemical Property of (3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

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Technology Process of (3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

There total 10 articles about (3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-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: 96.0%

: 184583-21-9
(3aS,8bR)-3-((S)-2-Bromo-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

: 184583-22-0
(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

Guidance literature:: With N,N,N',N'-tetramethylguanidinium azide; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/0957-4166(96)00385-0

Reference yield:

: 24273-36-7
(Z)-2-(hydroxyimino)-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

: 184583-22-0
(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaBH₄, 2.) pyridine / 1.) MeOH, 0 deg C, 3 h, 2.) 12 h

2: 100 percent / BH₃ / tetrahydrofuran / 3 h / Heating

4: 97 percent / K₂CO₃ / 7 h / Heating

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min

6: 1.) n-Bu₂BOTf, i-Pr₂NEt, 2.) NBS / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 1.5 h

7: 96 percent / 1,1,3,3-tetramethylguanidinium azide / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; N,N,N',N'-tetramethylguanidinium azide; di-n-butylboryl trifluoromethanesulfonate; borane; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0957-4166(96)00385-0

Reference yield:

: rac-cis-2-amino-3,3-dimethyl-2,3-dihydro-1H-inden-1-ol

: 184583-22-0
(3aS,8bR)-3-((R)-2-Azido-3-phenyl-propionyl)-4,4-dimethyl-3,3a,4,8b-tetrahydro-indeno[2,1-d]oxazol-2-one

Guidance literature:: Multi-step reaction with 5 steps

2: 97 percent / K₂CO₃ / 7 h / Heating

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min

4: 1.) n-Bu₂BOTf, i-Pr₂NEt, 2.) NBS / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 1.5 h

5: 96 percent / 1,1,3,3-tetramethylguanidinium azide / CH₂Cl₂ / 1 h / 0 °C

With N-Bromosuccinimide; n-butyllithium; N,N,N',N'-tetramethylguanidinium azide; di-n-butylboryl trifluoromethanesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/0957-4166(96)00385-0