(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

Base Information

Chemical Name:(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate
CAS No.:1574543-65-9
Molecular Formula:C₂₄H₂₅N₃O₃
Molecular Weight:403.481
Hs Code.:

Synonyms:(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

There total 28 articles about (4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate 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: 60.0%

: 1574543-64-8
(4aR,6S,7R,7aS)-diphenylmethyl 7-(tert-butoxycarbonylamino)-4-cyano-6-methoxymethoxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

: 1574543-65-9
(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

Guidance literature:: With bromocatecholborane; In dichloromethane; at 0 ℃; for 3.5h; Inert atmosphere;
DOI:10.1021/ol5002973

Reference yield:

: 1574543-50-2
(1S,2S,3aR,6aS)-allyl 2-hydroxy-1-hydroxymethyl-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylate

: 1574543-65-9
(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

Guidance literature:: Multi-step reaction with 23 steps

1.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

1.2: 12 h / 0 - 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / acetonitrile / 3 h / 50 °C

3.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0.25 h / -30 - 20 °C / Inert atmosphere

3.2: 0.17 h / -20 - 10 °C

4.1: ozone / dichloromethane; methanol / 0.08 h / -78 °C

4.2: 4 h / -78 - 20 °C / Inert atmosphere

5.1: CSA / methanol / 24 h / 20 °C / Inert atmosphere

6.1: sodium cyanoborohydride / tetrahydrofuran; formic acid / 4 h / 0 - 20 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

7.2: 2 h / -78 - 0 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 60 °C / Inert atmosphere

8.2: 0.5 h / 60 °C / Inert atmosphere

9.1: silica gel / tetrahydrofuran; benzene / 8 h / 60 °C / Inert atmosphere

10.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran; toluene / 12 h / 60 °C / Inert atmosphere

11.1: trichlorophosphate / 1 h / 0 - 20 °C / Inert atmosphere

12.1: dmap / acetonitrile / 2 h / 0 - 20 °C / Inert atmosphere

13.1: caesium carbonate; thiophenol / acetonitrile / 2 h / 0 °C / Inert atmosphere

14.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C / Molecular sieve; Inert atmosphere

15.1: sodium acetate; hydroxylamine hydrochloride / ethanol / 15 h / 20 °C / Inert atmosphere

16.1: acetic anhydride / 1 h / 80 °C

17.1: lithium hydroxide / tetrahydrofuran / 2 h / 0 - 20 °C

18.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

19.1: triethylamine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

19.2: 1 h / 0 °C / Inert atmosphere

20.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

21.1: triethylamine / dichloromethane; water; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

22.1: dichloromethane / 12 h / 20 °C

23.1: bromocatecholborane / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With pyrrolidine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; diphenyl phosphoryl azide; bromocatecholborane; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium acetate; acetic anhydride; silica gel; sodium cyanoborohydride; caesium carbonate; Dess-Martin periodane; ozone; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; formic acid; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 11.1: |Vilsmeier Reaction;
DOI:10.1021/ol5002973

Reference yield:

: 1574543-52-4
(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxamide

: 1574543-65-9
(4aR,6S,7R,7aS)-diphenylmethyl 7-amino-4-cyano-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylate

Guidance literature:: Multi-step reaction with 20 steps

1.1: ozone / dichloromethane; methanol / 0.08 h / -78 °C

1.2: 4 h / -78 - 20 °C / Inert atmosphere

2.1: CSA / methanol / 24 h / 20 °C / Inert atmosphere

3.1: sodium cyanoborohydride / tetrahydrofuran; formic acid / 4 h / 0 - 20 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 - 0 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 60 °C / Inert atmosphere

5.2: 0.5 h / 60 °C / Inert atmosphere

6.1: silica gel / tetrahydrofuran; benzene / 8 h / 60 °C / Inert atmosphere

7.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran; toluene / 12 h / 60 °C / Inert atmosphere

8.1: trichlorophosphate / 1 h / 0 - 20 °C / Inert atmosphere

9.1: dmap / acetonitrile / 2 h / 0 - 20 °C / Inert atmosphere

10.1: caesium carbonate; thiophenol / acetonitrile / 2 h / 0 °C / Inert atmosphere

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C / Molecular sieve; Inert atmosphere

12.1: sodium acetate; hydroxylamine hydrochloride / ethanol / 15 h / 20 °C / Inert atmosphere

13.1: acetic anhydride / 1 h / 80 °C

14.1: lithium hydroxide / tetrahydrofuran / 2 h / 0 - 20 °C

15.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

16.1: triethylamine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

16.2: 1 h / 0 °C / Inert atmosphere

17.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

18.1: triethylamine / dichloromethane; water; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

19.1: dichloromethane / 12 h / 20 °C

20.1: bromocatecholborane / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With dmap; diphenyl phosphoryl azide; bromocatecholborane; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium acetate; acetic anhydride; silica gel; sodium cyanoborohydride; caesium carbonate; Dess-Martin periodane; ozone; thiophenol; triethylamine; lithium hydroxide; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; formic acid; ethanol; dichloromethane; water; toluene; acetonitrile; benzene; 8.1: |Vilsmeier Reaction;
DOI:10.1021/ol5002973