(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

Base Information

Chemical Name:(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone
CAS No.:223675-90-9
Molecular Formula:C₂₀H₂₈BrNO₄
Molecular Weight:426.351
Hs Code.:

Synonyms:(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

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Chemical Property of (2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

Chemical Property:

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Technology Process of (2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

There total 23 articles about (2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone 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: 79.0%

: 223676-16-2
(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

: 223675-90-9
(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane;
DOI:10.1021/jo990877k

Reference yield:

: 223675-78-3
(R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanal

: 223675-90-9
(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

Guidance literature:: Multi-step reaction with 8 steps

1: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

2: 99 percent / HF / tetrahydrofuran; H₂O

3: 96 percent / PPh₃; CBr₄ / CH₂Cl₂

4: 70 percent / CAN / acetonitrile; H₂O / 2 h / 0 °C

5: CH₂Cl₂ / 3 h / 0 °C

6: LHMDS / tetrahydrofuran / 1 h / -78 °C

7: 32 percent / MCPBA / CH₂Cl₂ / -78 - 20 °C

8: 70 percent / PPh₃; CBr₄ / CH₂Cl₂

With ammonium cerium(IV) nitrate; carbon tetrabromide; hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Condensation / 2: Hydrolysis / 3: Cyclization / 4: Substitution / 5: Substitution / 6: Substitution / 7: Oxidation / 8: Substitution;
DOI:10.1021/jo990877k

Reference yield:

: 223676-04-8
(R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)pentanol

: 223675-90-9
(2'S,3'R)-1-[2'-(3'-benzyloxy)-1-(tert-butoxycarbonyl)piperidino]-3-bromo-2-propanone

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

3: 99 percent / HF / tetrahydrofuran; H₂O

4: 96 percent / PPh₃; CBr₄ / CH₂Cl₂

5: 70 percent / CAN / acetonitrile; H₂O / 2 h / 0 °C

6: CH₂Cl₂ / 3 h / 0 °C

7: LHMDS / tetrahydrofuran / 1 h / -78 °C

8: 32 percent / MCPBA / CH₂Cl₂ / -78 - 20 °C

9: 70 percent / PPh₃; CBr₄ / CH₂Cl₂

With oxalyl dichloride; ammonium cerium(IV) nitrate; carbon tetrabromide; hydrogen fluoride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: Cyclization / 5: Substitution / 6: Substitution / 7: Substitution / 8: Oxidation / 9: Substitution;
DOI:10.1021/jo990877k