(2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine

Base Information

• Chemical Name: (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine
• CAS No.: 366786-64-3
• Molecular Formula: C₂₀H₃₁NO₄
• Molecular Weight: 349.47
• Mol file: 366786-64-3.mol

Synonyms:(2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine

Chemical Property of (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine

There total 6 articles about (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine 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: 98.0%

methylmagnesium bromide (75-16-1) + (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-methoxycarbonyl-pyrrolidine (366786-63-2) → (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine (366786-64-3)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(01)00537-3

Reference yield:

(2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine (152612-42-5) → (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine (366786-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. sodium hypochlorite; KBr; TEMPO / acetone / 2 h / 0 °C

2: 924 mg / methanol; diethyl ether

3: 98 percent / diethyl ether; tetrahydrofuran / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; acetone;

DOI:10.1016/S0040-4020(01)00537-3

Reference yield:

[1-benzenesulfonylmethyl-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-carbamic acid tert-butyl ester → (2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine (366786-64-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: 2.31 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3.1: 92 percent / Na₂HPO₄; Na-Hg / methanol / 24 h / 0 °C

4.1: aq. sodium hypochlorite; KBr; TEMPO / acetone / 2 h / 0 °C

5.1: 924 mg / methanol; diethyl ether

6.1: 98 percent / diethyl ether; tetrahydrofuran / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; tetrabutyl ammonium fluoride; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; acetone;

DOI:10.1016/S0040-4020(01)00537-3

upstream raw materials:

methylmagnesium bromide

(2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-methoxycarbonyl-pyrrolidine

(2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine

(2R,5S)-5-(benzyloxymethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S,5R)-1-tert-butoxycarbonyl-2-hydroxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine