(1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine

Base Information

• Chemical Name: (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine
• CAS No.: 369379-18-0
• Molecular Formula: C₂₁H₂₅NO₇S₂
• Molecular Weight: 467.564
• Mol file: 369379-18-0.mol

Synonyms:(1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine

Chemical Property of (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine

There total 13 articles about (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine 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: 80.0%

(1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-[(4-methoxybenzyl)oxy]hexahydro-1H-pyrrolizine (369379-10-2) → (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine (369379-18-0)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 5h;

Reference yield:

(2S,4S)-4-(Buta-1,3-dienyl)-2-(4-methoxyphenyl)-1,3-dioxane → (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine (369379-18-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: DIBAL-H / CH₂Cl₂ / 1.5 h / 0 - 20 °C

1.2: 63 percent / I₂ / benzene / 1 h / 20 °C / UV-irradiation

2.1: 2.44 g / (COCl)2; DMSO; Et₃N / dimethylsulfoxide / 1.92 h / -60 °C

3.1: 2.67 g / aq. NaClO₂; NaH₂PO₄*H₂O; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 0.67 h / 0 - 20 °C

4.1: 2.32 g / pyridine / tetrahydrofuran / 20 h / 20 °C

5.1: 1.51 g / hydroxylamine hydrochloride; Et₃N / CH₂Cl₂ / 3 h / 20 °C

6.1: Bu₄NIO₄ / CHCl₃ / 2 h / 22 °C

7.1: 91 percent / Na(Hg); Na₂HPO₄ / ethanol / 14 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 0.83 h / 0 - 20 °C

9.1: 326 mg / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

10.1: 65 percent / aq. OsO₄; NMO / acetone / 30 h / 20 °C

11.1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 4 h / 20 °C

12.1: Et₃N / CH₂Cl₂ / 44 h / 20 °C

12.2: 21 percent / Pd(OH)2/C / methanol / 30 h / 20 °C

13.1: 80 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 20 °C

With pyridine; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; hydroxylamine hydrochloride; water; diisobutylaluminium hydride; tetrabutylammonium periodite; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; acetone; tert-butyl alcohol; 2.1: Swern oxidation;

Reference yield:

(E,S)-3-(4-Methoxybenzyloxy)hepta-4,6-dienal (369379-16-8) → (1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-hydroxyhexahydro-1H-pyrrolizine (369379-18-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 2.67 g / aq. NaClO₂; NaH₂PO₄*H₂O; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 0.67 h / 0 - 20 °C

2.1: 2.32 g / pyridine / tetrahydrofuran / 20 h / 20 °C

3.1: 1.51 g / hydroxylamine hydrochloride; Et₃N / CH₂Cl₂ / 3 h / 20 °C

4.1: Bu₄NIO₄ / CHCl₃ / 2 h / 22 °C

5.1: 91 percent / Na(Hg); Na₂HPO₄ / ethanol / 14 h / 0 °C

6.1: Et₃N / CH₂Cl₂ / 0.83 h / 0 - 20 °C

7.1: 326 mg / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

8.1: 65 percent / aq. OsO₄; NMO / acetone / 30 h / 20 °C

9.1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 4 h / 20 °C

10.1: Et₃N / CH₂Cl₂ / 44 h / 20 °C

10.2: 21 percent / Pd(OH)2/C / methanol / 30 h / 20 °C

11.1: 80 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 20 °C

With pyridine; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; 2-methyl-but-2-ene; dimethylsulfide borane complex; hydroxylamine hydrochloride; water; tetrabutylammonium periodite; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetone; tert-butyl alcohol;

upstream raw materials:

(1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-[(4-methoxybenzyl)oxy]hexahydro-1H-pyrrolizine

(E,S)-3-(4-Methoxybenzyloxy)hepta-4,6-dienal

(1S,7aS)-1-(4-Methoxybenzyloxy)-1,2,5,7a-tetrahydro-3H-pyrrolizin-3-one

(E,S)-3-(4-Methoxybenzyloxy)hepta-4,6-dien-1-ol