(1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine

Base Information

• Chemical Name: (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine
• CAS No.: 321887-52-9
• Molecular Formula: C₂₂H₂₇NO₃
• Molecular Weight: 353.461
• Mol file: 321887-52-9.mol

Synonyms:(1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine

Chemical Property of (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine

There total 11 articles about (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine 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: 70.0%

4-Nitro-benzoic acid (1R,6S,7S,7aS)-6-benzyloxy-7-benzyloxymethyl-hexahydro-pyrrolizin-1-yl ester → (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine (321887-52-9)

Guidance literature:

With water; potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 4h;

DOI:10.1021/jo0012187

Reference yield:

benzyl bromide (100-39-0) → (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine (321887-52-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.5 h

1.2: 86 percent / 1 h / 20 °C

2.1: 85 percent / H₂ / Lindlar catalyst / benzene / 0.67 h / 2068.65 Torr

3.1: 77 percent / CAN / acetonitrile / 1 h / 0 °C

4.1: 95 percent / NaH; nBu₄NI / tetrahydrofuran / 1 h / 20 °C

5.1: 90 percent / Grubbs catalyst / benzene / 12 h / Heating

6.1: 61 percent / NaHCO₃; m-CPBA / benzene / 36 h / 20 °C

7.1: 65 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

8.1: 70 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 16 h / 20 °C

9.1: 70 percent / K₂CO₃; H₂O / methanol; tetrahydrofuran / 4 h / 20 °C

With lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo0012187

Reference yield:

(3S,4S,5S)-3-hydroxy-4-hydroxymethyl-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone (321887-26-7) → (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine (321887-52-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.5 h

1.2: 86 percent / 1 h / 20 °C

2.1: 85 percent / H₂ / Lindlar catalyst / benzene / 0.67 h / 2068.65 Torr

3.1: 77 percent / CAN / acetonitrile / 1 h / 0 °C

4.1: 95 percent / NaH; nBu₄NI / tetrahydrofuran / 1 h / 20 °C

5.1: 90 percent / Grubbs catalyst / benzene / 12 h / Heating

6.1: 61 percent / NaHCO₃; m-CPBA / benzene / 36 h / 20 °C

7.1: 65 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

8.1: 70 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 16 h / 20 °C

9.1: 70 percent / K₂CO₃; H₂O / methanol; tetrahydrofuran / 4 h / 20 °C

With lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo0012187

upstream raw materials:

benzyl bromide

(3S,4S,5S)-3-hydroxy-4-hydroxymethyl-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

(1S,2S,7aR)-2-benzyloxy-1-benzyloxymethyl-2,5,7a-trihydropyrrolizin-3-one

(1aS,5S,6S,6aS,6bR)-5-benzyloxy-6-benzyloxymethylperhydrooxireno[2,3-a]pyrrolizin-4-one