(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

Base Information

Chemical Name:(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine
CAS No.:148020-06-8
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

Synonyms:(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

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Chemical Property of (2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

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Technology Process of (2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

There total 14 articles about (2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-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: 90.0%

: 108-24-7
acetic anhydride

: 148020-05-7
(2R,3S,4S)-3-Hydroxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

: 148020-06-8
(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

Guidance literature:: With triethylamine; for 8h; Ambient temperature;
DOI:10.1016/S0040-4020(01)86320-1

Reference yield:

: 148019-97-0
N-Acetyl-N-methyl-4-benzyloxy-3,4-bis<(methoxymethyl)oxy>butylamine

: 148020-06-8
(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) H₂, 2a.) (COCl)2, DMSO, 2b.) Et₃N / 1.) 10 percent Pd/C

2: 1.) butyllithium / 1.) THF, hexane, 0 deg C, 2.) THF, r.t.

3: KOH / methanol

4: 1.) BuLi, HMPA, 2.) -e / 1.) THF, hexane, -78 deg C, 5 min, 2.) -10 deg C

5: 82 percent / MeOH, conc. HCl, H₂O / 15 h / Heating

6: 85 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

7: 90 percent / Et₃N / 8 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; water; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86320-1

Reference yield:

: 1530-38-7
((4-methoxyphenyl)methyl)triphenylphosphonium bromide

: 148020-06-8
(2R,3S,4S)-3-Acetoxy-2-(4-methoxybenzyl)-1-methyl-4-<(tert-butyldimethylsilyl)oxy>-pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, r.t., overnight, 2.) THF, r.t., 2 h

2: KOH / methanol / 1 h / Ambient temperature

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C, 15 min

4: 2.) Na(CN)BH₃ / 1.) MeOH, 1 h, 2.) r.t., overnight

5: 1.) BuLi, HMPA, 2.) -e / 1.) THF, hexane, -78 deg C, 5 min, 2.) -10 deg C

6: 82 percent / MeOH, conc. HCl, H₂O / 15 h / Heating

7: 85 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

8: 90 percent / Et₃N / 8 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; water; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86320-1