(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

Base Information

Chemical Name:(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine
CAS No.:191092-18-9
Molecular Formula:C₂₂H₂₇NO₆S
Molecular Weight:433.525
Hs Code.:

Synonyms:(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

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Chemical Property of (2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

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Technology Process of (2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

There total 7 articles about (2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine 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: 94.0%

: 4124-41-8
p-toluenesulfonylanhydride

: 318511-13-6
(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-hydroxymethylpyrrolidine

: 191092-18-9
(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1248/cpb.48.1729

Reference yield:

: 33996-30-4
trans-4-hydroxy-L-proline ethyl ester hydrochloride

: 191092-18-9
(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / Et₃N / acetone; H₂O / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

2.2: 45 percent / Bu₄NI / tetrahydrofuran / 3 h / 20 °C

3.1: 91 percent / LiBH₄ / tetrahydrofuran / 7 h / 20 °C

4.1: 94 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

With lithium borohydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1248/cpb.48.1729

Reference yield:

: 40350-83-2,54631-82-2,54631-81-1
(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

: 191092-18-9
(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(p-toluenesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: HCl(g) / 2 h

2: Et₃N / acetone; H₂O / 3 h / 20 °C

3: 91 percent / LiBH₄ / tetrahydrofuran / 7 h / 20 °C

4: 94 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

With hydrogenchloride; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1248/cpb.48.1729