(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

Base Information

Chemical Name:(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine
CAS No.:156441-19-9
Molecular Formula:C₁₉H₃₃NO₂Si
Molecular Weight:335.562
Hs Code.:

Synonyms:(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

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Chemical Property of (2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

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Technology Process of (2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

There total 3 articles about (2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)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: 82.3%

: 156441-18-8
(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-vinylpyrrolidine

: 156441-19-9
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

Guidance literature:: (2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-vinylpyrrolidine; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 4h;

With sodium perborate; In tetrahydrofuran; water; at 20 ℃; for 12h;
DOI:10.1016/S0968-0896(99)00085-1

Reference yield:

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

: 156441-19-9
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -50 - 20 °C

2.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

2.2: 50.4 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

3.2: 82.3 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 2.1: Dehydrochlorination / 2.2: Wittig reaction / 3.1: hydroboration / 3.2: Oxidation;
DOI:10.1016/S0968-0896(99)00085-1

Reference yield:

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 156441-19-9
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-(2-hydroxyethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

1.2: 50.4 percent / tetrahydrofuran / 1 h / 0 - 5 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

2.2: 82.3 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

With potassium tert-butylate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1.1: Dehydrochlorination / 1.2: Wittig reaction / 2.1: hydroboration / 2.2: Oxidation;
DOI:10.1016/S0968-0896(99)00085-1