4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI)

Base Information

Chemical Name:4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI)
CAS No.:131944-39-3
Molecular Formula:C8H11NO4
Molecular Weight:185.17724
Hs Code.:
Mol file:131944-39-3.mol

Synonyms:4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI)

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Chemical Property of 4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI)

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Technology Process of 4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI)

There total 15 articles about 4H-Cyclopenta-1,3-dioxole-4-acetonitrile,tetrahydro-5,6-dihydroxy-,(3a-alpha-,4-bta-,5-bta-,6-bta-,6a-alpha-)-(9CI) 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:

: 29782-84-1
(1α,2α,3α)-cyclopent-4-en-1,2,3-triol

: 131944-39-3,139683-55-9
2α,3α-dihydroxy-4α,5α-(methylenedioxy)cyclopentane-1α-acetonitrile

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / 1 M HCl / 10 h / 60 °C

2: 88 percent / pyridine / DMAP / diethyl ether / 24 h / 1a) 0 deg C to r. t.

3: 1) lithium bis(trimethylsilyl)amide, 2) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone / 1) THF, -78 deg C, 10 min, 2a) -78 deg C, 3 h, b) up to -20 deg C

4: 90 percent / xylene / 18 h / 190 °C

5: 92 percent / I₂, KI, 0.5 M aq. NaHCO₃ / H₂O / 48 h

6: 1) DIBAL, 2) MgSO₄ / 1) CH₂Cl₂, hexane, -78 deg C, 5 min, 2) MeOH, up to r. t., 1 h

7: 89 percent / NH₂OH*HCl / H₂O; tetrahydrofuran

8: 75 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 3 h / Heating

9: 64 percent / DMAP / tetrahydrofuran / 2 h / 1a) -78 deg C to r. t.

10: NaH / tetrahydrofuran; paraffin / 168 h

11: 1) 1 M HCl, 2) K₂CO₃ / 1) THF, r. t., 15 min, 2) MeOH, r.t., 30 min

With pyridine; hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydroxylamine hydrochloride; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; potassium carbonate; 1,1'-carbonyldiimidazole; potassium iodide; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; water; paraffin; xylene;

Reference yield:

: 131944-28-0,139683-48-0
4α,5α-(methylenedioxy)cyclopent-2-en-1α-ol

: 131944-39-3,139683-55-9
2α,3α-dihydroxy-4α,5α-(methylenedioxy)cyclopentane-1α-acetonitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / pyridine / DMAP / diethyl ether / 24 h / 1a) 0 deg C to r. t.

2: 1) lithium bis(trimethylsilyl)amide, 2) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone / 1) THF, -78 deg C, 10 min, 2a) -78 deg C, 3 h, b) up to -20 deg C

3: 90 percent / xylene / 18 h / 190 °C

4: 92 percent / I₂, KI, 0.5 M aq. NaHCO₃ / H₂O / 48 h

5: 1) DIBAL, 2) MgSO₄ / 1) CH₂Cl₂, hexane, -78 deg C, 5 min, 2) MeOH, up to r. t., 1 h

6: 89 percent / NH₂OH*HCl / H₂O; tetrahydrofuran

7: 75 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 3 h / Heating

8: 64 percent / DMAP / tetrahydrofuran / 2 h / 1a) -78 deg C to r. t.

9: NaH / tetrahydrofuran; paraffin / 168 h

10: 1) 1 M HCl, 2) K₂CO₃ / 1) THF, r. t., 15 min, 2) MeOH, r.t., 30 min

With pyridine; hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydroxylamine hydrochloride; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; potassium carbonate; 1,1'-carbonyldiimidazole; potassium iodide; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; water; paraffin; xylene;

Reference yield:

: 16329-18-3
3β,5β-dibromocyclopentane-1α,2α-diyl dibenzoate

: 131944-39-3,139683-55-9
2α,3α-dihydroxy-4α,5α-(methylenedioxy)cyclopentane-1α-acetonitrile

Guidance literature:: Multi-step reaction with 12 steps

1: 1) NaHCO₃, 2) NaOMe / 1) DMSO, 100 deg C, 1.5 h, 2) MeOH, r. t., 1 h

2: 89 percent / 1 M HCl / 10 h / 60 °C

3: 88 percent / pyridine / DMAP / diethyl ether / 24 h / 1a) 0 deg C to r. t.

4: 1) lithium bis(trimethylsilyl)amide, 2) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone / 1) THF, -78 deg C, 10 min, 2a) -78 deg C, 3 h, b) up to -20 deg C

5: 90 percent / xylene / 18 h / 190 °C

6: 92 percent / I₂, KI, 0.5 M aq. NaHCO₃ / H₂O / 48 h

7: 1) DIBAL, 2) MgSO₄ / 1) CH₂Cl₂, hexane, -78 deg C, 5 min, 2) MeOH, up to r. t., 1 h

8: 89 percent / NH₂OH*HCl / H₂O; tetrahydrofuran

9: 75 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 3 h / Heating

10: 64 percent / DMAP / tetrahydrofuran / 2 h / 1a) -78 deg C to r. t.

11: NaH / tetrahydrofuran; paraffin / 168 h

12: 1) 1 M HCl, 2) K₂CO₃ / 1) THF, r. t., 15 min, 2) MeOH, r.t., 30 min

With pyridine; hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hydroxylamine hydrochloride; iodine; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; potassium carbonate; 1,1'-carbonyldiimidazole; potassium iodide; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; water; paraffin; xylene;