6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester
CAS No.:343565-21-9
Molecular Formula:C₁₉H₂₂N₂O₃
Molecular Weight:326.395
Hs Code.:

6-oxo-1,5,6,8,9,11a-hexahydro-2<i>H</i>,4<i>H</i>-1,5-methano-pyrido[1,2-<i>a</i>][1,5]diazocine-3-carboxylic acid benzyl ester

Synonyms:6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

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Chemical Property of 6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

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Technology Process of 6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

There total 7 articles about 6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester 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: 72.0%

: 343565-19-5
(1R,4ξ,5S)-7-benzyloxycarbonyl-4-hydroxy-3-[(Z)-1-trimethylsilyl-1-buten-4-yl]-3,7-diazabicyclo[3.3.1]nonan-2-one

: 343565-21-9
6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

Guidance literature:: With trifluoroacetic acid; at 0 ℃; for 6h;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6

Reference yield:

: 206554-22-5
(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester

: 343565-21-9
6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: KMnO₄ / 2-methyl-propan-2-ol; aq. phosphate buffer / 1 h / 20 °C / pH 7.2

2: 85 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

3: 98 percent / NaOH / methanol / 24 h / 20 °C

4: 62 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

5: 69 mg / K₂CO₃ / methanol / 1 h / Heating

6: 72 percent / trifluoroacetic acid / 6 h / 0 °C

With sodium hydroxide; potassium permanganate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; phosphate buffer; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6

Reference yield:

: 206761-38-8
(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

: 343565-21-9
6-oxo-1,5,6,8,9,11a-hexahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 0.25 h / -60 °C

1.2: 2.7 g / triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

2.1: KMnO₄ / 2-methyl-propan-2-ol; aq. phosphate buffer / 1 h / 20 °C / pH 7.2

3.1: 85 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

4.1: 98 percent / NaOH / methanol / 24 h / 20 °C

5.1: 62 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / 20 °C

6.1: 69 mg / K₂CO₃ / methanol / 1 h / Heating

7.1: 72 percent / trifluoroacetic acid / 6 h / 0 °C

With sodium hydroxide; potassium permanganate; oxalyl dichloride; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; phosphate buffer; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6