3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

Base Information

Chemical Name:3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol
CAS No.:124217-25-0
Molecular Formula:C₁₉H₂₇NO₂
Molecular Weight:301.429
Hs Code.:

Synonyms:3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

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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 3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

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Technology Process of 3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

There total 11 articles about 3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol 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: 65.0%

: 124217-15-8
trans-7-(cyclobutylmethyl)octahydro-4a-(3-methoxyphenyl)-2H-pyrano<2,3-c>pyridine

: 124217-25-0
3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

Guidance literature:: With lithium methanethiolate; In N,N-dimethyl-formamide; at 130 - 150 ℃;
DOI:10.1039/P19890001187

Reference yield:

: 73224-22-3
1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine

: 124217-25-0
3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

Guidance literature:: Multi-step reaction with 10 steps

2: 1)(COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, - 60 deg C, 15 min; 2) CH₂Cl₂, -20 deg C

3: 1) NaH / 1) DMF, r.t., 3 h, 2) DMF,r.t., 45 min

5: 1)CH₃SO₂Cl, Et₃N, 2) NaH / 1) CH₂Cl₂, -10 deg C, 0.5 h; 2) DMF, 70 deg C, 3 h

6: K₂CO₃ / 1,2-dichloro-ethane / 3.5 h / Heating

7: 2M HCL / methanol / 3.5 h / Heating

8: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

9: 1) LiAlH₄, 2) aq. Na₂SO₄, 2M NaOH / 1) THF, reflux, overnight; 2) THF, heating

10: 65 percent / LiSMe / dimethylformamide / 130 - 150 °C

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; lithium methanethiolate; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; sodium sulfate; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1039/P19890001187

Reference yield:

: 124216-72-4
trans-4-(3-methoxyphenyl)-1-methylpiperidin-3-ol

: 124217-25-0
3-((4aR,8aS)-7-Cyclobutylmethyl-hexahydro-pyrano[2,3-c]pyridin-4a-yl)-phenol

Guidance literature:: Multi-step reaction with 9 steps

1: 1)(COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, - 60 deg C, 15 min; 2) CH₂Cl₂, -20 deg C

2: 1) NaH / 1) DMF, r.t., 3 h, 2) DMF,r.t., 45 min

4: 1)CH₃SO₂Cl, Et₃N, 2) NaH / 1) CH₂Cl₂, -10 deg C, 0.5 h; 2) DMF, 70 deg C, 3 h

5: K₂CO₃ / 1,2-dichloro-ethane / 3.5 h / Heating

6: 2M HCL / methanol / 3.5 h / Heating

7: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

8: 1) LiAlH₄, 2) aq. Na₂SO₄, 2M NaOH / 1) THF, reflux, overnight; 2) THF, heating

9: 65 percent / LiSMe / dimethylformamide / 130 - 150 °C

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; lithium methanethiolate; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; sodium sulfate; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1039/P19890001187