(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

Base Information

Chemical Name:(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile
CAS No.:635299-84-2
Molecular Formula:C₁₉H₃₀N₂OSi
Molecular Weight:330.545
Hs Code.:

Synonyms:(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

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Chemical Property of (3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

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Technology Process of (3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

There total 4 articles about (3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile 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: 51.0%

: 2408-36-8
lithium cyanide

: 154343-02-9
(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

: 635299-84-2
(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

: 635299-83-1
(2S,4R)-[1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl]acetonitrile

Guidance literature:: (2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin; With triethylamine; Methanesulfonic anhydride; In chloroform; at 0 ℃; for 3h;

lithium cyanide; In chloroform; N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1016/j.tetasy.2003.08.020

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 635299-84-2
(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

2.1: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3.1: Et₃N; Ms₂O / CHCl₃ / 3 h / 0 °C

3.2: 18 percent / CHCl₃; dimethylformamide / 24 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2003.08.020

Reference yield:

: 154342-88-8
(2S,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate

: 635299-84-2
(3R,5R)-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine-3-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / imidazole / dimethylformamide / 10 h / 0 - 20 °C

2.1: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3.1: Et₃N; Ms₂O / CHCl₃ / 3 h / 0 °C

3.2: 18 percent / CHCl₃; dimethylformamide / 24 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2003.08.020