(2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine

Base Information

• Chemical Name: (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine
• CAS No.: 849402-62-6
• Molecular Formula: C₂₅H₃₄N₂O₄
• Molecular Weight: 426.556
• Mol file: 849402-62-6.mol

Synonyms:(2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine

Chemical Property of (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine

There total 2 articles about (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine 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: 69.0%

(2R,3S,4S)-1-benzyl-4-benzylaminomethyl-3-hydroxy-2-hydroxymethylpyrrolidine (849402-57-9) + di-tert-butyl dicarbonate (24424-99-5) → (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine (849402-62-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.3987/COM-04-S(P)13

Reference yield:

(3aS,3bR,6R,7aR)-2-benzyl-1,2,3a,3b,4,7a-hexahydro-6-phenyl-3,5-dioxa-2,6a-diazacyclopentapentalen-7-one (160823-80-3) → (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine (849402-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 17 h / Heating

2: 69 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.3987/COM-04-S(P)13

Reference yield: 42.0%

(2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine (849402-62-6) → (3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine (849402-63-7)

Guidance literature:

(2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine; With trifluoroacetic anhydride; In tetrahydrofuran; at -78 ℃; for 3h;

With triethylamine; for 17h; Heating;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.3987/COM-04-S(P)13

upstream raw materials:

(2R,3S,4S)-1-benzyl-4-benzylaminomethyl-3-hydroxy-2-hydroxymethylpyrrolidine

di-tert-butyl dicarbonate

(3aS,3bR,6R,7aR)-2-benzyl-1,2,3a,3b,4,7a-hexahydro-6-phenyl-3,5-dioxa-2,6a-diazacyclopentapentalen-7-one

Downstream raw materials:

(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

(3S,4S,5S)-1-benzyl-5-benzylaminomethyl-3,4-dihydroxypiperidine