N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide

Base Information

• Chemical Name: N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide
• CAS No.: 791608-05-4
• Molecular Formula: C₃₁H₃₄N₂O₆
• Molecular Weight: 530.621

Synonyms:N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide

Chemical Property of N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide

There total 10 articles about N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide 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: 86.0%

(6R,7R,8R,8aR)-7,8-Bis-benzyloxy-6-(4-methoxy-benzylamino)-hexahydro-oxazolo[3,4-a]pyridin-3-one (791608-03-2) + acetyl chloride (75-36-5) → N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide (791608-05-4)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃;

DOI:10.1002/anie.200453863

Reference yield:

(S)-1-[(R)-2-oxooxazolidin-4-yl]allyl benzoate (791607-96-0) → N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide (791608-05-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 81 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: 99 percent / Grubbs catalyst / toluene / 20 °C

3.1: 85 percent / K₂CO₃ / methanol / 20 °C

4.1: 91 percent / NaH / dimethylformamide / 0 - 20 °C

5.1: 90 percent / (DHQD)2Phal; K₂CO₃; CH₃SO₂NH₂ / K₃[Fe(CN)6]; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: nBu₂SnO / toluene / Heating

6.2: 69 percent / Bu₄NBr / toluene / 100 °C

7.1: 86 percent / (COCl)2; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / -70 - 20 °C

8.1: 78 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

9.1: 86 percent / pyridine; 4-dimethylaminopyridine / 0 - 20 °C

With pyridine; dmap; oxalyl dichloride; methanesulfonamide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; potassium osmate(VI); Grubbs catalyst first generation; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 7.1: Swern oxidation;

DOI:10.1002/anie.200453863

Reference yield:

[(2S,3S)-3-vinyloxiran-2-yl]methyl benzoylcarbamate (791607-94-8) → N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide (791608-05-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / K₂CO₃; (C₈H₁₇)3CH₃NCl / CH₂Cl₂; H₂O / 20 °C

2.1: 81 percent / NaH / dimethylformamide / 0 - 20 °C

3.1: 99 percent / Grubbs catalyst / toluene / 20 °C

4.1: 85 percent / K₂CO₃ / methanol / 20 °C

5.1: 91 percent / NaH / dimethylformamide / 0 - 20 °C

6.1: 90 percent / (DHQD)2Phal; K₂CO₃; CH₃SO₂NH₂ / K₃[Fe(CN)6]; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

7.1: nBu₂SnO / toluene / Heating

7.2: 69 percent / Bu₄NBr / toluene / 100 °C

8.1: 86 percent / (COCl)2; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / -70 - 20 °C

9.1: 78 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

10.1: 86 percent / pyridine; 4-dimethylaminopyridine / 0 - 20 °C

With pyridine; dmap; oxalyl dichloride; methanesulfonamide; (C₈H₁₇)3CH₃NCl; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; potassium osmate(VI); Grubbs catalyst first generation; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 8.1: Swern oxidation;

DOI:10.1002/anie.200453863

upstream raw materials:

(6R,7R,8R,8aR)-7,8-Bis-benzyloxy-6-(4-methoxy-benzylamino)-hexahydro-oxazolo[3,4-a]pyridin-3-one

acetyl chloride

(S)-1-[(R)-2-oxooxazolidin-4-yl]allyl benzoate

[(2S,3S)-3-vinyloxiran-2-yl]methyl benzoylcarbamate

Downstream raw materials:

N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-1-phenethyl-piperidin-3-yl)-acetamide

N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide

N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

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