tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate
• CAS No.: 1393106-22-3
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48
• Mol file: 1393106-22-3.mol

Synonyms:tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate

Chemical Property of tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate

There total 12 articles about tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-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: 78.0%

tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-oxopiperidine-1-carboxylate (1393106-20-1) → tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate (1393106-22-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -75 - -20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201200377

Reference yield:

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine (1241959-30-7) → tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate (1393106-22-3)

Guidance literature:

Multi-step reaction with 11 steps

1: triethylamine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux; Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / -75 °C / Inert atmosphere

5: water; sodium hydroxide / methanol / 3 h / 0 - 20 °C / Inert atmosphere

6: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7: potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / -10 °C / Inert atmosphere

8: boron trifluoride diethyl etherate / tetrahydrofuran; acetone / 1 h / 5 - 20 °C / Cooling with ice

9: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere

10: Dess-Martin periodane / dichloromethane / 3 h / Inert atmosphere

11: sodium tetrahydroborate / ethanol / 3 h / -75 - -20 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; potassium osmate(VI) dihydrate; sodium tetrahydroborate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 4: Mitsunobu reaction;

DOI:10.1002/ejoc.201200377

Reference yield:

tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393105-88-8) → tert-butyl 2-(benzyloxymethyl)-3,4-O-isopropylidene-5-hydroxypiperidine-1-carboxylate (1393106-22-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / -10 °C / Inert atmosphere

3: boron trifluoride diethyl etherate / tetrahydrofuran; acetone / 1 h / 5 - 20 °C / Cooling with ice

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere

5: Dess-Martin periodane / dichloromethane / 3 h / Inert atmosphere

6: sodium tetrahydroborate / ethanol / 3 h / -75 - -20 °C / Inert atmosphere

With 1H-imidazole; potassium osmate(VI) dihydrate; sodium tetrahydroborate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.201200377

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

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