(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

Base Information

Chemical Name:(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine
CAS No.:182000-81-3
Molecular Formula:C₂₁H₂₉NO₂
Molecular Weight:327.467
Hs Code.:

Synonyms:(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

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Chemical Property of (3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

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Technology Process of (3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

There total 11 articles about (3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine 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: 76.0%

: 182000-60-8
[(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile

: 182000-81-3
(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

Guidance literature:: With silver nitrate; In ethanol; Ambient temperature;
DOI:10.1021/ja961640y

Reference yield:

: 123190-88-5
(R)-2-(S)-Pyrrolidin-2-yl-1-(2-trimethylsilanyl-ethoxymethoxy)-propan-2-ol

: 182000-81-3
(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

3: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

4: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5: 1.) ClTi(O-i-Pr)3 / 1.) THF, -50 deg C

6: 76 percent / AgNO₃ / ethanol / Ambient temperature

With triisopropoxytitanium(IV) chloride; lithium tetrafluoroborate; oxalyl dichloride; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y

Reference yield:

: 123190-86-3
(1R,7aS)-tetrahydro-1-methyl-1-(hydroxymethyl)-1H,3H-pyrrolo<1,2-c>oxazol-3-one

: 182000-81-3
(3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 14 h / Ambient temperature

2: aq. KOH / ethanol / 16 h / 80 °C

3: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 91 percent / KH / tetrahydrofuran / 0.5 h / Heating

5: 78 percent / aq. LiBF₄ / acetonitrile / 2 h / 70 °C

6: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.) ClTi(O-i-Pr)3 / 1.) THF, -50 deg C

8: 76 percent / AgNO₃ / ethanol / Ambient temperature

With triisopropoxytitanium(IV) chloride; potassium hydroxide; lithium tetrafluoroborate; oxalyl dichloride; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ja961640y