1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI)

Base Information

• Chemical Name: 1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI)
• CAS No.: 103979-75-5
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.181
• Mol file: 103979-75-5.mol

Synonyms:1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI)

Chemical Property of 1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI)

Chemical Property:

• PSA: 37.38000
• LogP: 0.13410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI)

There total 18 articles about 1H-Pyrrolizine-1-carboxaldehyde, hexahydro-3-oxo-, (1R-cis)- (9CI) 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:

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → (1R,7aS)-hexahydro-3-oxo-3H-pyrrolizine-1-carbaldehyde (103979-75-5,146405-72-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / 4M NaOH

2: 90 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -60 °C

3: 75 percent / sodium methylsulphinylmethylide / dimethylsulfoxide; tetrahydrofuran

4: aq. NaOH / ethane-1,2-diol / Heating

5: Et₃N / diethyl ether

6: 100 percent / NaIO₄ / methanol; H₂O

7: 87 percent / (CF₃CO)2O / CH₂Cl₂ / Ambient temperature

8: NaIO₄ / methanol; H₂O

9: Al, H₂O / tetrahydrofuran

10: OsO₄, NaIO₄ / H₂O; tetrahydrofuran

With sodium hydroxide; sodium periodate; aluminum amalgam; osmium(VIII) oxide; oxalyl dichloride; water; sodium methylsulfinylmethanide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethylene glycol; dimethyl sulfoxide;

DOI:10.1039/c39860000654

Reference yield:

(S)-1-<(phenylthio)acetyl>pyrrolidine-2-methanol (122030-79-9) → (1R,7aS)-hexahydro-3-oxo-3H-pyrrolizine-1-carbaldehyde (103979-75-5,146405-72-3)

Guidance literature:

Multi-step reaction with 8 steps

1: SO₃-pyridine, triethylamine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

2: diisopropylethylamine (DIPEA), LiCl / acetonitrile / 2 h / Ambient temperature

3: N-chlorosuccinimide (NCS) / CCl₄ / 1 h / Ambient temperature

4: Bu₃SnH, azobisisobutyronitrile (AIBN) / toluene / 2 h / Heating

5: 79 percent / Raney Ni / ethanol / 6 h / Heating

6: tetrahydrofuran; diethyl ether / 0.17 h / -78 °C

7: methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

8: 1.) ozone, 2.) CH₃SCH₃ / 1.) methanol, -78 deg C, 30 min, 2.) methanol, RT, overnight

With N-chloro-succinimide; pyridine-SO₃ complex; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ozone; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; nickel; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1248/cpb.40.2308

Reference yield:

(S)-1-(2-Phenylsulfanyl-acetyl)-pyrrolidine-2-carbaldehyde (122030-56-2) → (1R,7aS)-hexahydro-3-oxo-3H-pyrrolizine-1-carbaldehyde (103979-75-5,146405-72-3)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropylethylamine (DIPEA), LiCl / acetonitrile / 2 h / Ambient temperature

2: N-chlorosuccinimide (NCS) / CCl₄ / 1 h / Ambient temperature

3: Bu₃SnH, azobisisobutyronitrile (AIBN) / toluene / 2 h / Heating

4: 79 percent / Raney Ni / ethanol / 6 h / Heating

5: tetrahydrofuran; diethyl ether / 0.17 h / -78 °C

6: methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

7: 1.) ozone, 2.) CH₃SCH₃ / 1.) methanol, -78 deg C, 30 min, 2.) methanol, RT, overnight

With N-chloro-succinimide; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ozone; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; nickel; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1248/cpb.40.2308

upstream raw materials:

(1S,7aS)-hexahydro-1-(2,2-didphenylethenyl)-3H-pyrrolizin-3-one

(1S,7aS)-1-vinyltetrahydro-1H-pyrrolizin-3(2H)-one

ethyl (2S)-2-(hyroxymethyl)pyrrolidine-1-carboxylate

(S)-(-)-1-ethoxycarbonylpyrrolidine-2-carbaldehyde

Downstream raw materials:

laburnine

Refernces

• 1、 Sato,Tsujimoto,Matsubayashi,Ishibashi,Ikeda. "Carbamoylmethyl radical cyclization: Formal synthesis of (-)-trachelanthamidine". . p. 2308 - 2312. Retrieved 2007/10/02.