(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester
• CAS No.: 724787-54-6
• Molecular Formula: C₁₈H₂₆N₂O₅
• Molecular Weight: 350.415
• Mol file: 724787-54-6.mol

Synonyms:(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester

Chemical Property of (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester

There total 7 articles about (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-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: 14.0%

di-tert-butyl dicarbonate (24424-99-5) + (1S,6R)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester (1624258-63-4) → benzyl (3S,4S)-3,4-trans-3-[(tert-butoxycarbonyl)amino]-4-hydroxypiperidine-1-carboxylate (1052715-77-1,859854-67-4,1549812-60-3) + (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester (724787-54-6)

Guidance literature:

(1S,6R)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester; With ammonium hydroxide; In ethanol; water; at 20 ℃; for 48h;

di-tert-butyl dicarbonate; In dichloromethane; at 20 ℃;

Reference yield:

1,2,3,6-tetrahydropyridine (694-05-3) → (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester (724787-54-6) + C18H26N2O5 (724787-53-5)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / water / 18 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C

3: sodium azide; ammonium chloride / methanol; water / 18 h / 65 °C

4: palladium on activated charcoal; hydrogen / ethyl acetate / 22 h / 20 °C / 760.05 Torr

5: dichloromethane / 18 h / 20 °C

With sodium azide; palladium on activated charcoal; hydrogen; sodium hydrogencarbonate; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.bmcl.2011.09.117

Reference yield:

3,4-epoxy-piperidine-1-carboxylic acid benzyl ester (66207-08-7,1624258-63-4) → (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxypiperidine-1-carboxylic acid benzyl ester (724787-54-6) + C18H26N2O5 (724787-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide; ammonium chloride / methanol; water / 18 h / 65 °C

2: palladium on activated charcoal; hydrogen / ethyl acetate / 22 h / 20 °C / 760.05 Torr

3: dichloromethane / 18 h / 20 °C

With sodium azide; palladium on activated charcoal; hydrogen; ammonium chloride; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.bmcl.2011.09.117

upstream raw materials:

di-tert-butyl dicarbonate

(1S,6R)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester

1,2,3,6-tetrahydropyridine

3,4-epoxy-piperidine-1-carboxylic acid benzyl ester