(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

Base Information

Chemical Name:(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol
CAS No.:110005-24-8
Molecular Formula:C₁₈H₃₄NO₄PS
Molecular Weight:391.512
Hs Code.:

Synonyms:(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

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Chemical Property of (2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

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Technology Process of (2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

There total 10 articles about (2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol 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: 91.0%

: 110005-23-7
(2S-cis)-4-(diphenylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

: 110005-24-8
(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

Guidance literature:: With hydrogen; rhodium on alumina; In methanol; at 150 ℃; for 48h; under 114000 Torr;
DOI:10.1016/S0040-4039(00)84983-7

Reference yield:

: 110005-19-1
(2S-trans)-4-hydroxy-1-(methylsulfonyl)-2-pyrrolidinemethanol

: 110005-24-8
(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

Guidance literature:: Multi-step reaction with 6 steps

1: 4-dimethylaminopyridine, Et₃N / tetrahydrofuran / 16 h / Ambient temperature

2: 92 percent / anh. pyridine / 15 h / Ambient temperature

3: 70 percent / tetrahydrofuran; dioxane / a) 0 deg C, 2 h, b) RT, overnight

4: 10percent aq. H₂O₂ / methanol / a) 0 deg C, 1 h, b) RT, 1 h

5: HCl gas / methanol / 2 h / Ambient temperature

6: 91 percent / H₂, 5percent Rh on Al₂O₃ powder / methanol / 48 h / 150 °C / 114000 Torr

With pyridine; hydrogenchloride; dmap; rhodium on alumina; hydrogen; dihydrogen peroxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol;
DOI:10.1248/cpb.42.481

Reference yield:

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

: 110005-24-8
(2S-cis)-4-(dicyclohexylphosphinyl)-1-(methylsulfonyl)-2-pyrrolidinemethanol

Guidance literature:: Multi-step reaction with 8 steps

1: 79 percent / anh. pyridine / a) 0 deg C, 6 h, b) RT, 15 h

2: 87 percent / LiAlH₄ / tetrahydrofuran / a) 0 deg C, 3 h, b) RT, 3 h

3: 4-dimethylaminopyridine, Et₃N / tetrahydrofuran / 16 h / Ambient temperature

4: 92 percent / anh. pyridine / 15 h / Ambient temperature

5: 70 percent / tetrahydrofuran; dioxane / a) 0 deg C, 2 h, b) RT, overnight

6: 10percent aq. H₂O₂ / methanol / a) 0 deg C, 1 h, b) RT, 1 h

7: HCl gas / methanol / 2 h / Ambient temperature

8: 91 percent / H₂, 5percent Rh on Al₂O₃ powder / methanol / 48 h / 150 °C / 114000 Torr

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; rhodium on alumina; hydrogen; dihydrogen peroxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol;
DOI:10.1248/cpb.42.481