(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

Base Information

Chemical Name:(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide
CAS No.:256393-09-6
Molecular Formula:C₂₅H₃₇NO₅S
Molecular Weight:463.638
Hs Code.:

Synonyms:(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

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Chemical Property of (1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

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Technology Process of (1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

There total 4 articles about (1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide 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: 70.0%

: 163182-10-3
(1S,2S)-N,N-diisopropyl [2-spiro-2'-(1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

: 256393-09-6
(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

Guidance literature:: (1S,2S)-N,N-diisopropyl [2-spiro-2'-(1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -100 ℃; for 0.5h;

benzyl halide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ol9910666

Reference yield: 60.0%

: 163182-10-3
(1S,2S)-N,N-diisopropyl [2-spiro-2'-(1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

: 256393-09-6
(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

Guidance literature:: (1S,2S)-N,N-diisopropyl [2-spiro-2'-(1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -100 - -45 ℃; for 1.83333h;

With oxalic acid; In tetrahydrofuran; water; at 0 ℃; pH=6 - 7; Product distribution / selectivity;

Reference yield:

: 256393-05-2
(1S)-N,N-diisopropyl (2,2-dimethoxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide

: 256393-09-6
(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-phenylmethyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 74 percent / BF₃*OEt₂ / diethyl ether / -50 - -45 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -100 °C

2.2: 70 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 °C

With boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane;
DOI:10.1021/ol9910666