tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate
CAS No.:908599-40-6
Molecular Formula:C₂₂H₃₅NO₇S
Molecular Weight:457.588
Hs Code.:

Synonyms:tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

There total 13 articles about tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate 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: 80.0%

: 908599-39-3
tert-butyl (2R,3S)-2-(3-hydroxypropyl)-3-methoxymethoxypiperidine-1-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 908599-40-6
tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

Guidance literature:: With pyridine; at 20 ℃; for 1.5h;
DOI:10.1021/jm0601809

Reference yield:

: 908599-33-7
(R)-2-Dibenzylamino-pentane-1,5-diol

: 908599-40-6
tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 56 percent / imidazole / CH₂Cl₂ / 0 °C

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3: tetrahydrofuran / -50 - 20 °C

4: aq. HCl / acetone / 4 h / 20 °C

5: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

6: Et₃N / methanol / 1 h / 20 °C

7: 55 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

8: iPr₂NEt / 1,2-dimethoxy-ethane / 15 h / 50 °C

9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

10: 80 percent / pyridine / 1.5 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetone;
DOI:10.1021/jm0601809

Reference yield:

: (R)-2-Dibenzylamino-pentanedioic acid

: 908599-40-6
tert-butyl (2R,3S)-3-methoxymethoxy-2-[3-(p-toluenesulfonyloxy)propyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: LiAlH₄ / tetrahydrofuran / 0 °C

2: 56 percent / imidazole / CH₂Cl₂ / 0 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: tetrahydrofuran / -50 - 20 °C

5: aq. HCl / acetone / 4 h / 20 °C

6: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

7: Et₃N / methanol / 1 h / 20 °C

8: 55 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

9: iPr₂NEt / 1,2-dimethoxy-ethane / 15 h / 50 °C

10: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

11: 80 percent / pyridine / 1.5 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetone;
DOI:10.1021/jm0601809