((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

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Chemical Name:((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone
CAS No.:201946-61-4
Molecular Formula:C₁₃H₁₅NO₃
Molecular Weight:233.267
Hs Code.:

Synonyms:((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

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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 ((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

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Technology Process of ((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

There total 7 articles about ((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone 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: 76.0%

: 201946-60-3
Acetic acid (2R,3S)-2-acetoxymethyl-1-benzoyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

: 201946-61-4
((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

Guidance literature:: With potassium cyanide; In methanol; at 25 ℃; for 18h;
DOI:10.1021/jo971706n

Reference yield:

: 201946-53-4
N-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-N-trimethylsilanylmethyl-benzamide

: 201946-61-4
((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

2: 87 percent / aq. HF / acetonitrile / 0.5 h / 25 °C

3: 93 percent / 4-DMAP / pyridine / 17 h / 25 °C

4: 46 percent / (NH₄)2Ce(NO₃)6 / acetonitrile / 20 h / 40 °C

5: 76 percent / KCN / methanol / 18 h / 25 °C

With dmap; potassium cyanide; n-butyllithium; ammonium cerium(IV) nitrate; hydrogen fluoride; In pyridine; methanol; acetonitrile;
DOI:10.1021/jo971706n

Reference yield:

: 201946-52-3
N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-N-trimethylsilanylmethyl-benzamide

: 201946-61-4
((2R,3S)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridin-1-yl)-phenyl-methanone

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, 25 deg C, 2.5 h

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

3: 87 percent / aq. HF / acetonitrile / 0.5 h / 25 °C

4: 93 percent / 4-DMAP / pyridine / 17 h / 25 °C

5: 46 percent / (NH₄)2Ce(NO₃)6 / acetonitrile / 20 h / 40 °C

6: 76 percent / KCN / methanol / 18 h / 25 °C

With dmap; potassium cyanide; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; hydrogen fluoride; dimethyl sulfoxide; triethylamine; In pyridine; methanol; acetonitrile;
DOI:10.1021/jo971706n