2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol

Base Information

• Chemical Name: 2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol
• CAS No.: 900513-88-4
• Molecular Formula: C17H25NO2
• Molecular Weight: 275.391
• Mol file: 900513-88-4.mol

Synonyms:2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol;(1R,2R)-2-((R)-3-(benzyloxy)pyrrolidin-1-yl)cyclohexanol

Chemical Property of 2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol

Chemical Property:

• Boiling Point: 400.8±45.0 °C(Predicted)
• PKA: 14.95±0.40(Predicted)
• PSA: 32.70000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 2.51890

Purity/Quality:

98% min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol

There total 17 articles about 2-(3-Benzyloxy-pyrrolidin-1-yl)-cyclohexanol 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: 56.0%

2-(3-benzyloxy-pyrrolidin-1-yl)-cyclohexanol → (1R,2R)-2-[(R)-3-(benzyloxy)pyrrolidin-1-yl]cyclohexanol (900513-88-4) + 2S-(3R-benzyloxy-pyrrolidin-1S-yl)-cyclohexanol N-oxide (906802-28-6)

Guidance literature:

2-(3-benzyloxy-pyrrolidin-1-yl)-cyclohexanol; With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In dichloromethane; at 20 ℃; for 0.5h;

With tert.-butylhydroperoxide; In dichloromethane; at -30 - -10 ℃; for 2.5h;

Reference yield:

(+/-)-trans-2-aminocyclohexanol (931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5,931-15-7) → (1R,2R)-2-[(R)-3-(benzyloxy)pyrrolidin-1-yl]cyclohexanol (900513-88-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide / water / 3.5 h / 0 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 8 h / 5 - 20 °C

3.1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C / 760.05 Torr

4.1: potassium iodide / N,N-dimethyl-formamide / 2 h / 20 °C

4.2: 6 h / 105 °C

5.1: sodium hydroxide / tetrahydrofuran; water / 8 h / 20 °C

6.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 10 h / 20 °C

7.1: hydrogenchloride / methanol; water / 0.5 h / 20 °C

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere

8.2: 0 °C

8.3: pH Ca_. 1

With 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 5%-palladium/activated carbon; hydrogen; dicyclohexyl-carbodiimide; potassium iodide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0031-1289619

Reference yield:

(1R,2R)-2-[(3R)-3-benzyloxy-1-pyrrolidinyl]cyclohexanol 0.5 di-p-toluoyl-L-tartarate → (1R,2R)-2-[(R)-3-(benzyloxy)pyrrolidin-1-yl]cyclohexanol (900513-88-4)

Guidance literature:

With sodium hydroxide; In water; toluene; at 26 ℃;

upstream raw materials:

cyclohexene oxide

(R)-4-(benzyloxy)-1-[(1R,2R)-2-(tert-butyldimethylsiloxy)cyclohexyl]pyrrolidin-2-one

ethyl (R)-3-(benzyloxy)-4-chlorobutanoate

(+/-)-trans-2-aminocyclohexanol

Downstream raw materials:

(3R)-3-benzyloxy-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl}pyrrolidine

C₂₇H₃₇NO₅

C₂₇H₃₇NO₅