(1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

Base Information

• Chemical Name: (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one
• CAS No.: 129415-99-2
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.335

Synonyms:(1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

Chemical Property of (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

There total 23 articles about (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one 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: 80.0%

(1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (129416-16-6,129446-81-7) → (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one (129415-99-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; at 75 ℃;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

5-(3-Methoxy-phenyl)-oxazolidin-2-one (129416-01-9) → (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one (129415-99-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 90 percent / KH / tetrahydrofuran

2: 4 N NaOH / ethanol / Heating

3: DMAP, iPr₂NEt / CH₂Cl₂

4: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

5: tetrahydrofuran / 60 °C

6: 1 N HCl / tetrahydrofuran

7: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

8: 88 percent / iPrNEt₂ / CH₂Cl₂

9: RedAl / tetrahydrofuran / -78 to -50 deg C

10: PPTS

11: Bu₄NF / tetrahydrofuran

12: Swern oxidation

13: KH / tetrahydrofuran; triethylamine / 0 °C

14: 48 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / 0 deg C to room temperature

15: 81 percent / RhCl(PPh₃)3 / toluene / Heating

16: 1.) O₃, 2.) Me₂S / MeOH

17: NaHCO₃

18: 84 percent / NaBH₄ / methanol

19: SOCl₂, pyridine

20: DBU / toluene / Heating

21: 80 percent / H₂, HCl / Pd-C / ethanol / 75 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; triethylamine; toluene;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

2-Allylamino-1-(3-methoxy-phenyl)-ethanol → (1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one (129415-99-2)

Guidance literature:

Multi-step reaction with 19 steps

1: DMAP, iPr₂NEt / CH₂Cl₂

2: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

3: tetrahydrofuran / 60 °C

4: 1 N HCl / tetrahydrofuran

5: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

6: 88 percent / iPrNEt₂ / CH₂Cl₂

7: RedAl / tetrahydrofuran / -78 to -50 deg C

8: PPTS

9: Bu₄NF / tetrahydrofuran

10: Swern oxidation

11: KH / tetrahydrofuran; triethylamine / 0 °C

12: 48 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / 0 deg C to room temperature

13: 81 percent / RhCl(PPh₃)3 / toluene / Heating

14: 1.) O₃, 2.) Me₂S / MeOH

15: NaHCO₃

16: 84 percent / NaBH₄ / methanol

17: SOCl₂, pyridine

18: DBU / toluene / Heating

19: 80 percent / H₂, HCl / Pd-C / ethanol / 75 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; triethylamine; toluene;

DOI:10.1016/0040-4039(90)80083-X

upstream raw materials:

(1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

5-(3-Methoxy-phenyl)-oxazolidin-2-one

(tert-Butyl-dimethyl-silanyloxy)-(3-methoxy-phenyl)-acetonitrile

3-Allyl-5-(3-methoxy-phenyl)-oxazolidin-2-one

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