tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate
• CAS No.: 1393106-15-4
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 1393106-15-4.mol

Synonyms:tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Chemical Property of tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

There total 16 articles about tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-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: 90.0%

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (1241959-32-9) → tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393106-15-4)

Guidance literature:

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h; Cooling with ice;

With water;

DOI:10.1002/ejoc.201200377

Reference yield: 80.0%

C18H23NO4 → tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393106-15-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0 ℃;

DOI:10.1039/c4ra04558k

Reference yield:

C15H20O3 → tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393106-15-4)

Guidance literature:

Multi-step reaction with 10 steps

1: potassium hexacyanoferrate(III); potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; osmium(VIII) oxide; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 °C

2: triethylamine; dmap / dichloromethane / 5 h

3: sodium azide / N,N-dimethyl-formamide / 18 h / 80 °C

4: palladium(II) hydroxide; hydrogen / methanol / 3 h / 20 °C / 1551.49 Torr

5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C

6: triethylamine; dmap / tetrahydrofuran / 20 °C

7: triphenylphosphine; 1H-imidazole; iodine / toluene / 0.5 h / 120 °C / Inert atmosphere

8: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux

9: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux

10: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 °C

With 1H-imidazole; dmap; selenium(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; methanesulfonamide; cerium(III) chloride heptahydrate; hydrogen; iodine; palladium(II) hydroxide; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: |Sharpless Asymmetric Epoxidation;

DOI:10.1039/c4ra04558k

upstream raw materials:

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

tert-butyl (2S,3R,4S,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-(tert-butyldiphenylsilyloxy)pyridine-1(2H)-carboxylate