6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one

Base Information

• Chemical Name: 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one
• CAS No.: 122695-52-7
• Molecular Formula: C₁₄H₁₇NO₂S
• Molecular Weight: 263.36
• Mol file: 122695-52-7.mol

Synonyms:6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one

Chemical Property of 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one

There total 12 articles about 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one 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: 89.0%

(S)-5-Oxo-1-phenylsulfanyl-hexahydro-pyrrolizine-1-carboxylic acid methyl ester (122695-51-6,132288-57-4) → (S)-7-Hydroxymethyl-7-phenylsulfanyl-hexahydro-pyrrolizin-3-one (103979-82-4,103979-84-6,122695-52-7,132341-51-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; start. mat. is not opt. pure;

DOI:10.1016/S0040-4039(00)82286-8

Reference yield: 78.5%

6-ethoxycarbonyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one (103979-81-3,103979-83-5) → 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one (122695-52-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 2h;

Reference yield:

4-(2-Oxo-5-phenylsulfanyl-pyrrolidin-1-yl)-butyric acid ethyl ester (103979-78-8) → 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one (122695-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) HCO₂Et, NaH, 2.) p-TsN₃, Et₃N / 1.) C₆H₆, 0 deg C to r.t., 2.) CH₂Cl₂, 0 deg C

2: 55 percent / Rh₂(OAc)4 / benzene / 0.25 h / Heating

3: LiAlH₄ / diethyl ether / 0 °C

With dirhodium tetraacetate; lithium aluminium tetrahydride; 4-toluenesulfonyl azide; sodium hydride; triethylamine; formic acid ethyl ester; In diethyl ether; benzene;

DOI:10.1039/c39860000651

upstream raw materials:

(S)-5-Oxo-1-phenylsulfanyl-hexahydro-pyrrolizine-1-carboxylic acid methyl ester

1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione

2-(2,5-dioxopyrrolidin-1-yl)ethyl acetate

1-(2-acetoxyethyl)-5-acetoxy-2-pyrrolidinone

Downstream raw materials:

6-hydroxymethyl-6-phenylsulphinyl-1-azabicyclo<3.3.0>octan-2-one

7-(hydroxymethyl)-1,2,5,7a-tetrahydro-3H-pyrrolizin-3-one

(+)-supinidine

(-)-supinidine