(2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine

Base Information

• Chemical Name: (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine
• CAS No.: 132430-78-5
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.321
• Mol file: 132430-78-5.mol

Synonyms:(2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine

Chemical Property of (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine

There total 16 articles about (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)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:

(S)-Pyroglutaminol (17342-08-4) → (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine (132430-78-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, DMF, RT, 1h, 2.) RT, 20h

2: 1.) lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, -78 deg C, 5 min

3: 81 percent / 30percent H₂O₂ / ethyl acetate / 0.5 h / 15 - 20 °C

4: 11 percent / OsO₄, N-methylmorpholine N-oxide*H₂O / acetone; H₂O / 14 h / Ambient temperature

5: 90 percent / p-TsOH / acetone / 2 h / Ambient temperature

6: 86 percent / H₂ / Pd black / ethanol / 13 h / 760 Torr / Ambient temperature

7: 72 percent / borane-Me₂S complex / tetrahydrofuran / 1 h / 70 °C

8: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) CH₂Cl₂, -20 deg C, 2.) -20 deg C

With osmium(VIII) oxide; oxalyl dichloride; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; palladium; In tetrahydrofuran; ethanol; water; ethyl acetate; acetone;

DOI:10.1248/cpb.38.2712

Reference yield:

(S)-1-benzyl-5-benzyloxymethyl-2-oxo-3-pyrroline (113571-61-2) → (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine (132430-78-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 11 percent / OsO₄, N-methylmorpholine N-oxide*H₂O / acetone; H₂O / 14 h / Ambient temperature

2: 90 percent / p-TsOH / acetone / 2 h / Ambient temperature

3: 86 percent / H₂ / Pd black / ethanol / 13 h / 760 Torr / Ambient temperature

4: 72 percent / borane-Me₂S complex / tetrahydrofuran / 1 h / 70 °C

5: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) CH₂Cl₂, -20 deg C, 2.) -20 deg C

With osmium(VIII) oxide; oxalyl dichloride; dimethylsulfide borane complex; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium; In tetrahydrofuran; ethanol; water; acetone;

DOI:10.1248/cpb.38.2712

Reference yield:

(R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone (101758-68-3) → (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine (132430-78-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 52 percent / OsO₄, N-methylmorpholine N-oxide*H₂O / acetone; H₂O / Ambient temperature

2: 80 percent / p-TsOH / acetone / Ambient temperature

3: 84 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

4: 91 percent / pyridine / 13 h / 0 °C

5: 51 percent / NaN₃ / dimethylformamide / 0.42 h / 140 - 145 °C

6: 65 percent / H₂ / Pd black / ethanol / 14 h / 760 Torr / Ambient temperature

7: 100 percent / K₂CO₃ / acetone / 1 h / Ambient temperature

8: 80 percent / conc. HCl / methanol / 14 h / Ambient temperature

9: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) CH₂Cl₂, -20 deg C, 2.) -20 deg C

With pyridine; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.38.2712

upstream raw materials:

(2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol

benzyl bromide

(3S,4S,5R)-1-benzyl-5-hydroxymethyl-3,4-isopropylidenedioxy-2-pyrrolidinone

(S)-1-benzyl-5-benzyloxymethyl-2-oxo-3-pyrroline

Downstream raw materials:

(R)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol

(S)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol

(3aS,4R,6aR)-5-Benzyl-4-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

(3aS,4R,6aR)-5-Benzyl-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole