isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate

Base Information

• Chemical Name: isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate
• CAS No.: 345223-64-5
• Molecular Formula: C₁₂H₂₁NO₂
• Molecular Weight: 211.304
• Mol file: 345223-64-5.mol

Synonyms:

Chemical Property of isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate

There total 1 articles about isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate 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%

isopropyl alcohol (67-63-0,8013-70-5) + 6'-methoxycinchonidone (84-31-1) → 6-methoxyquinoline-4-carboxylic acid (86-68-0) + isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate (345223-64-5)

Guidance literature:

isopropyl alcohol; With potassium tert-butylate; oxygen; In tetrahydrofuran; at 0 ℃; for 1h;

6'-methoxycinchonidone; With oxygen; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja9100276

Reference yield:

isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate (345223-64-5) → 7-(2-benzyloxy-ethyl)-3,4,4a,5,6,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (345223-69-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 0 - 20 °C

2.1: 95 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylsulfoxide; tetrahydrofuran / 20 °C

5.1: 96 percent / Cl₂(PCy₃)2RuCHPh / CH₂Cl₂ / 20 °C

6.1: Sia₂BH / tetrahydrofuran / 6 h / -10 - 4 °C

6.2: 70 percent / NaOH aq.; 30 percent H₂O₂ / tetrahydrofuran / 18 h / -10 - 20 °C

7.1: 92 percent / NaH; n-Bu₄NI; 18-c-6 / tetrahydrofuran / 19 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; Grubbs catalyst first generation; 18-crown-6 ether; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(01)00404-X

Reference yield:

isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate (345223-64-5) → (4aR,7R,8R,8aR)-7-(2-Benzyloxy-ethyl)-7,8-dihydroxy-octahydro-isoquinoline-2-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 8 steps

1.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 0 - 20 °C

2.1: 95 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylsulfoxide; tetrahydrofuran / 20 °C

5.1: 96 percent / Cl₂(PCy₃)2RuCHPh / CH₂Cl₂ / 20 °C

6.1: Sia₂BH / tetrahydrofuran / 6 h / -10 - 4 °C

6.2: 70 percent / NaOH aq.; 30 percent H₂O₂ / tetrahydrofuran / 18 h / -10 - 20 °C

7.1: 92 percent / NaH; n-Bu₄NI; 18-c-6 / tetrahydrofuran / 19 h / 0 - 20 °C

8.1: 83 percent / K₂OsO₂(OH)4; (DHQD)2PHAL; MsNClNa / propan-1-ol; H₂O / 17 h / 20 °C

With dmap; lithium aluminium tetrahydride; Grubbs catalyst first generation; potassium dioxotetrahydroxoosmate(VI); 18-crown-6 ether; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; N-chloromethanesulfonamide sodium salt; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; propan-1-ol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(01)00404-X

upstream raw materials:

isopropyl alcohol

6'-methoxycinchonidone

Downstream raw materials:

7-(2-benzyloxy-ethyl)-3,4,4a,5,6,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester