(2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate

Base Information

• Chemical Name: (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate
• CAS No.: 304665-09-6
• Molecular Formula: C₂₃H₂₇NO₃
• Molecular Weight: 365.472
• Mol file: 304665-09-6.mol

Synonyms:(2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate

Chemical Property of (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate

There total 27 articles about (2R,3S)-benzyl 2-allyl-3-(benzyloxy) 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: 95.0%

(2R,3S)-2-allyl-3-(benzyloxy)piperidine + benzyl chloroformate (501-53-1,94274-21-2) → (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate (304665-09-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2020.152151

Reference yield: 87.0%

benzyl bromide (100-39-0) + (2R,3S)-benzyl 2-allyl-3-hydroxypiperidine-1-carboxylate (625437-86-7,244056-94-8) → (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate (304665-09-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1055/s-2003-40988

Reference yield:

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one (221015-46-9) → (2R,3S)-benzyl 2-allyl-3-(benzyloxy) piperidine-1-carboxylate (304665-09-6)

Guidance literature:

Multi-step reaction with 18 steps

1: 90 percent / NaBH₄; CeCl₃ / methanol / 0 °C

2: H₂ / PtO₂

3: Et₃N

4: NaN₃ / dimethylformamide / Heating

5: LiAlH₄ / tetrahydrofuran

6: K₂CO₃

7: 90 percent / NaH / dimethylformamide

8: TBAF / tetrahydrofuran

9: Et₃N

10: LiI / tetrahydrofuran

11: Zn; AcOH / ethanol

12: 94 percent / NaBH₄ / ethanol

13: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid

14: H₂ / PtO₂

15: Bu₃P; Py

16: NaH

17: H₂O₂ / H₂O

18: CaCO₃ / diphenyl ether / Heating

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; acetic acid; triethylamine; calcium carbonate; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; diphenylether; ethanol; water; N,N-dimethyl-formamide; 1: Reduction / 2: Catalytic hydrogenation / 3: Substitution / 4: Substitution / 5: Reduction / 6: Substitution / 7: Substitution / 8: desilylation / 9: Substitution / 10: Substitution / 11: Reduction / 12: Reduction / 13: Cyclization / 14: Catalytic hydrogenation / 15: Substitution / 16: Substitution / 17: Oxidation / 18: Elimination;

DOI:10.1021/ol006384f

upstream raw materials:

benzyl bromide

(2R,3S)-benzyl 2-allyl-3-hydroxypiperidine-1-carboxylate

(3S)-1-(4-methoxybenzyl)-3-hydroxypiperidine-2,6-dione

(5S)-6-allyl-5-(tert-butyldimethylsilyloxy)piperidin-2-one

Downstream raw materials:

febrifugine

(2R,3S)-3-Benzyloxy-2-oxiranylmethyl-piperidine-1-carboxylic acid benzyl ester

(2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

(2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester