(1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester

Base Information

• Chemical Name: (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester
• CAS No.: 365223-89-8
• Molecular Formula: C₃₃H₄₆N₂O₄
• Molecular Weight: 534.739

Synonyms:(1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester

Chemical Property of (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester

Chemical Property:

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Technology Process of (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester

There total 6 articles about (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester 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: 46.0%

(1R,2S,5R)-menthyl chloroformate (14602-86-9,7635-53-2) + 1,5,7-Trimethyl-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-2-one → (1S,5S,7R)-(1,5,7)-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester (365223-91-2) + (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester (365223-89-8)

Guidance literature:

1,5,7-Trimethyl-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(1R,2S,5R)-menthyl chloroformate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1.75h;

DOI:10.1055/s-2001-15231

Reference yield:

3-amino-5,6,7,8-tetrahydro-2-naphthalenol (28094-04-4) → (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester (365223-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / pyridine / tetrahydrofuran / 16 h / Heating

2.1: 87 percent / pyridine; SOCl₂ / benzene / 3 h / Heating

3.1: NaBH₄ / ethanol / 15 h / 20 °C

3.2: 88 percent / triethylsilane / trifluoroacetic acid / 4 h / 20 °C

4.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 46 percent / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; thionyl chloride; In tetrahydrofuran; ethanol; hexane; benzene;

DOI:10.1055/s-2001-15231

Reference yield:

(1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride (109216-50-4) → (1R,5R,7S)-1,5,7-Trimethyl-2-oxo-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-3-carboxylic acid (-)-menthyl ester (365223-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / pyridine / tetrahydrofuran / 16 h / Heating

2.1: 87 percent / pyridine; SOCl₂ / benzene / 3 h / Heating

3.1: NaBH₄ / ethanol / 15 h / 20 °C

3.2: 88 percent / triethylsilane / trifluoroacetic acid / 4 h / 20 °C

4.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 46 percent / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; thionyl chloride; In tetrahydrofuran; ethanol; hexane; benzene;

DOI:10.1055/s-2001-15231

upstream raw materials:

(1R,2S,5R)-menthyl chloroformate

3-amino-5,6,7,8-tetrahydro-2-naphthalenol

(1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride

1,5,7-Trimethyl-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-2,4-dione

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