3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

Base Information

Chemical Name:3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile
CAS No.:1613394-09-4
Molecular Formula:C₁₇H₁₈FN₃OS
Molecular Weight:331.414
Hs Code.:

Synonyms:3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

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Chemical Property of 3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

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Technology Process of 3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

There total 10 articles about 3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile 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: 64.0%

: 1613394-20-9
N-[(4aR,6R,8aS)-8a-(5-cyano-2-fluorophenyl)-6-cyclopropyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

: 1613394-09-4
3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

Guidance literature:: With hydrazine hydrate; In ethanol; at 20 ℃;

Reference yield:

: 1613394-10-7
[1-(2,2-diethoxyethoxy)but-3-en-1-yl]cyclopropane

: 1613394-09-4
3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

Guidance literature:: Multi-step reaction with 9 steps

1.1: hydrogenchloride; water / tetrahydrofuran / 15.5 h / 20 - 40 °C

2.1: sodium acetate; hydroxylamine hydrochloride / ethanol; water / 0.25 h

2.2: 1 h / 60 °C

3.1: sodium hypochlorite; triethylamine / dichloromethane / 19.5 - 22.8 °C

4.1: ChiralPAK? AS-H / methanol / Resolution of racemate

5.1: boron trifluoride diethyl etherate / toluene / 0.25 h / -78 °C

5.2: 0.08 h / -78 °C

5.3: 1.25 h / -78 °C

6.1: zinc; acetic acid / 20 °C

7.1: dichloromethane / 0 - 20 °C

8.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1.5 h / -50 - 0 °C

9.1: hydrazine hydrate / ethanol / 20 °C

With pyridine; hydrogenchloride; sodium hypochlorite; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; water; sodium acetate; hydrazine hydrate; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene;

Reference yield:

: (±)-(3aR,5R)-5-cyclopropyl-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole

: 1613394-09-4
3-[(4aR,6R,8aS)-2-amino-6-cyclopropyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-4-fluorobenzonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: ChiralPAK? AS-H / methanol / Resolution of racemate

2.1: boron trifluoride diethyl etherate / toluene / 0.25 h / -78 °C

2.2: 0.08 h / -78 °C

2.3: 1.25 h / -78 °C

3.1: zinc; acetic acid / 20 °C

4.1: dichloromethane / 0 - 20 °C

5.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1.5 h / -50 - 0 °C

6.1: hydrazine hydrate / ethanol / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; hydrazine hydrate; acetic acid; zinc; In methanol; ethanol; dichloromethane; toluene;