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

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Chemical Name:(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyano-4-phenylsulfonylcyclohexyl)pyrrolidine
CAS No.:442887-09-4
Molecular Formula:C₂₈H₄₄N₂O₅SSi
Molecular Weight:548.819
Hs Code.:

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

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

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

There total 8 articles about (2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-cyano-4-phenylsulfonylcyclohexyl)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: 74.9%

: 7605-28-9
2-(phenylsulfonyl)acetonitrile

: 871024-86-1
1,1'-azodicarbonyl-dipiperidine

: 442681-37-0
(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(1,5-pentanediol-3-yl)pyrrolidine

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

Guidance literature:: With trimethylphosphane; In tetrahydrofuran; at 50 ℃; for 13h;
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

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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; sodium hydride; acetic acid; triphenylphosphine; sodium chloride; trimethylphosphane; In tetrahydrofuran; pyridine; 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

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

Guidance literature:: Multi-step reaction with 5 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

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