(2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

Base Information

Chemical Name:(2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine
CAS No.:220458-80-0
Molecular Formula:C₁₉H₂₃NO₂
Molecular Weight:297.397
Hs Code.:

Synonyms:

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Chemical Property of (2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

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Technology Process of (2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

There total 16 articles about (2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine 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:

: Toluene-4-sulfonic acid (3S,4R)-4-benzylamino-5-benzyloxy-3-hydroxy-pentyl ester

: 220458-80-0
(2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

Guidance literature:: With potassium carbonate; In ethanol; for 3h; Yield given; Heating;
DOI:10.3987/com-98-8292

Reference yield:

: 100-39-0
benzyl bromide

: 220458-80-0
(2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / NaH, Bu₄NI / tetrahydrofuran / 20 h / 0 - 20 °C

2: 1.) disiamylborane; 2.) aq. NaOH, 30 percent H₂O₂ / 1.) THF, r.t., 20 h; 2.) THF, 0 deg C, 2 h then r.t., 2 h

3: aq. KOH / aq. ethanol / 24 h / Heating

4: 80 percent / H₂O; diethyl ether / 0 deg C, 2 h then r.t., 20 h

5: 57 percent / pyridine, i-Pr₂NEt / CHCl₃ / 0 deg C, 2 h then r.t., 36 h

6: TFA / CH₂Cl₂ / 3 h / Ambient temperature

7: K₂CO₃ / aq. ethanol / 3 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water;
DOI:10.3987/com-98-8292

Reference yield:

: 91510-85-9
phenyl 2,3;5,6-di-O-isopropylidene-1-thio-α-D-mannofuranoside

: 220458-80-0
(2R,3S)-1-benzyl-2-benzyloxymethyl-3-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 15 steps

1: 80 percent / sat. aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 20 h / Ambient temperature

2: 86 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C, 1 h then r.t., 2 h

3: 85 percent / potassium t-butoxide / tetrahydrofuran / 0 deg C, 1 h then r.t., 20 h

4: H₅IO₆ / ethyl acetate / 3 h / Ambient temperature

5: 97 percent / NaBH₄ / aq. ethanol / 0 deg C, 15 min then r.t., 30 min

6: 78 percent / Ph₃P, iodine / toluene; CH₂Cl₂; pyridine / 4 h / 80 °C

7: Zn/Ag / tetrahydrofuran / 1 h / 65 °C

8: 90 percent / sodium borohydride / tetrahydrofuran; aq. ethanol / 0 deg C, 2 h then r.t., overnight

9: 86 percent / NaH, Bu₄NI / tetrahydrofuran / 20 h / 0 - 20 °C

10: 1.) disiamylborane; 2.) aq. NaOH, 30 percent H₂O₂ / 1.) THF, r.t., 20 h; 2.) THF, 0 deg C, 2 h then r.t., 2 h

11: aq. KOH / aq. ethanol / 24 h / Heating

12: 80 percent / H₂O; diethyl ether / 0 deg C, 2 h then r.t., 20 h

13: 57 percent / pyridine, i-Pr₂NEt / CHCl₃ / 0 deg C, 2 h then r.t., 36 h

14: TFA / CH₂Cl₂ / 3 h / Ambient temperature

15: K₂CO₃ / aq. ethanol / 3 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; dihydrogen peroxide; iodine; silver; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; periodic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; toluene;
DOI:10.3987/com-98-8292