(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

Base Information

Chemical Name:(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine
CAS No.:442887-13-0
Molecular Formula:C₂₂H₄₀N₂O₃Si
Molecular Weight:408.657
Hs Code.:

Synonyms:(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

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Chemical Property of (2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

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Technology Process of (2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

There total 9 articles about (2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)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: 97.5%

: 442887-09-4
(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyano-4-phenylsulfonylcyclohexyl)pyrrolidine

: 442887-13-0
(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

Guidance literature:: With magnesium; mercury dichloride; In tetrahydrofuran; methanol; at 18 ℃; for 1h;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 442681-67-6
(2R,4R)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-13-0
(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: PPh₃; diisopropyl azodicarboxylate; AcOH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 82.2 percent / aq. NaOH / ethanol / 0.17 h / 20 °C

2.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: TBAB / tetrahydrofuran / 24 h / 50 °C

4.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

5.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

6.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

7.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

With 1H-imidazole; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; sodium hydride; magnesium; acetic acid; triphenylphosphine; sodium chloride; mercury dichloride; trimethylphosphane; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.2: Michael addition;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 442681-68-7
(2R,4S)-1-tert-butoxycarbonyl-2-[(E)-2-(ethoxycarbonyl)vinyl]-4-hydroxypyrrolidine

: 442887-13-0
(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyanocyclohexyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 78.9 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: TBAB / tetrahydrofuran / 24 h / 50 °C

3.1: 27.94 percent / NaCl / dimethylsulfoxide; H₂O / 3 h / 160 °C

4.1: 9.09 g / LiAlH₄ / pyridine / 0.5 h / -20 °C

5.1: 74.9 percent / Me₃P / tetrahydrofuran / 13 h / 50 °C

6.1: 97.5 percent / HgCl₂; Mg / tetrahydrofuran; methanol / 1 h / 18 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium hydride; magnesium; sodium chloride; mercury dichloride; trimethylphosphane; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.2: Michael addition;
DOI:10.1016/S0968-0896(01)00430-8