tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate

Base Information

• Chemical Name: tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate
• CAS No.: 143949-29-5
• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.398
• Mol file: 143949-29-5.mol

Synonyms:tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate

Chemical Property of tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate

There total 3 articles about tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-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:

tert-butyl <1R-(1α,2β,3α,4α)>-3-bromobicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-28-4) + benzyl alcohol (100-51-6,185532-71-2) → tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-29-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 3h; Yield given;

DOI:10.1016/S0040-4039(00)61322-9

Reference yield:

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (144016-17-1) → tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

2: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

With sulfuric acid; sodium hydride; In dichloromethane;

DOI:10.1248/cpb.42.854

Reference yield:

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (127658-15-5) → tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-29-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.57 g / 2N aq. NaOH / 1,2-dimethoxy-ethane; methanol / 1 h / 0 °C

2: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

3: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

With sodium hydroxide; sulfuric acid; sodium hydride; In methanol; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1248/cpb.42.854

upstream raw materials:

tert-butyl <1R-(1α,2β,3α,4α)>-3-bromobicyclo<2.2.1>hept-5-ene-2-carboxylate

benzyl alcohol

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

Downstream raw materials:

(3R,5S)-2-[3-Benzenesulfonyl-2-(1-benzenesulfonyl-1H-pyrrol-3-yl)-2-hydroxy-propyl]-3,5-dimethyl-cyclopentanone

methyl (3R,5S)-3,5-dimethyl-1-cyclopentenecarboxylate

tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate

(3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester