(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

Base Information

Chemical Name:(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate
CAS No.:627100-77-0
Molecular Formula:C₁₉H₃₃NO₄SSi
Molecular Weight:399.627
Hs Code.:

Synonyms:(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

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Technology Process of (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

There total 6 articles about (3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate 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%

: 124-63-0
methanesulfonyl chloride

: 154343-00-7
(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-ol

: 627100-77-0
(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

Guidance literature:: With triethylamine; In chloroform; at -10 ℃; for 2h;
DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

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

: 627100-77-0
(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / CHCl₃ / 6 h / Heating

1.2: 12.40 g / aq. NaOH / CHCl₃ / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3.1: 38 percent / imidazole / dimethylformamide / 1 h / 0 °C

4.1: 80 percent / Et₃N / CHCl₃ / 2 h / -10 °C

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2003.08.019

Reference yield:

: 100-39-0
benzyl bromide

: 627100-77-0
(3R,5S)-1-benzyl-5-(tert-butyldimethylsilyloxymethyl)pyrrolidin-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / CHCl₃ / 6 h / Heating

1.2: 12.40 g / aq. NaOH / CHCl₃ / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3.1: 38 percent / imidazole / dimethylformamide / 1 h / 0 °C

4.1: 80 percent / Et₃N / CHCl₃ / 2 h / -10 °C

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2003.08.019