benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

Base Information

Chemical Name:benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate
CAS No.:343565-26-4
Molecular Formula:C₂₁H₂₆N₂O₅
Molecular Weight:386.448
Hs Code.:

Synonyms:benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

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Chemical Property of benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

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Technology Process of benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

There total 3 articles about benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate 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: 80.0%

: 14044-63-4
but-3-yn-1-amine

: 251346-98-2
(3R,5S)-3-carboxyl-5-acetoxymethylpiperidine-1-carboxylic acid benzyl ester

: 343565-26-4
benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In acetonitrile; at 25 ℃; for 12h;
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

: 343565-26-4
benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 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: 80 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

With potassium permanganate; oxalyl dichloride; benzotriazol-1-ol; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In 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:

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

: 343565-26-4
benzyl (3R,5S)-5-acetoxymethyl-3-[(3-butynyl)carbamoyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 80 percent / DCC; HOBt / acetonitrile / 12 h / 25 °C

With potassium permanganate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In phosphate buffer; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1099-0690(200104)2001:7<1377::aid-ejoc1377>3.3.co;2-6