(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester
CAS No.:1203455-33-7
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

There total 11 articles about (2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-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: 49.0%

: C₂₁H₂₉NO₆

: 1203455-33-7
(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

Guidance literature:: C₂₁H₂₉NO₆; With ammonium cerium (IV) nitrate; In acetonitrile; for 0.833333h; Reflux;

With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 0.25h; diastereoselective reaction;
DOI:10.1016/j.tetlet.2018.03.035

Reference yield:

: 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol

: 1203455-33-7
(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

2.2: 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetic acid / 24 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 - 20 °C / Inert atmosphere

5.1: L-proline; Nitrosobenzene / dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

5.2: 20 h / 20 °C / Inert atmosphere

6.1: ammonium cerium (IV) nitrate / acetonitrile / 0.83 h / Reflux

6.2: 0.25 h / 20 °C

With 1H-imidazole; n-butyllithium; ammonium cerium (IV) nitrate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; Nitrosobenzene; L-proline; In tetrahydrofuran; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; acetonitrile; 5.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetlet.2018.03.035

Reference yield:

: 866488-35-9
(E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

: 1091605-50-3
(2R,3S)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

: 1203455-33-7
(2S,3R)-3-hydroxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 0.166667h; Overall yield = 73 %; Overall yield = 131 mg; diastereoselective reaction;
DOI:10.1016/j.tet.2017.07.041