(1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• CAS No.: 136992-56-8
• Molecular Formula: C₃₉H₅₁NO₇
• Molecular Weight: 645.836
• Mol file: 136992-56-8.mol

Synonyms:

Chemical Property of (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

There total 14 articles about (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl 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:

(2-bromo-3-methoxyphenyl)acetic acid (54639-89-3) → (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (136992-56-8)

Guidance literature:

Multi-step reaction with 12 steps

1: diethyl ether / 1 h / 0 °C

2: 1.) LDA, N,N,N',N'-tetramethylethylenediamine / 1.) THF, hexane, -78 deg C, 1h, then -78 deg C, 30 min; 2.) THF, -78 deg C, 2 h

3: Jones-reagent / acetone / 0.33 h / Ambient temperature

4: water, sodium chloride / dimethylsulfoxide / 2 h / 140 °C

5: 88 percent / methanol / 10 h / Ambient temperature

6: 62 percent / dl-camphorsulfonic acid / methanol / 1 h / Heating

7: 79 percent / n-butyllithium / hexane; diethyl ether / 1 h / -78 °C

8: pyridine, chromium (VI) oxide, celite / CH₂Cl₂ / 1 h / Ambient temperature

9: 1M hydrochloric acid / tetrahydrofuran; H₂O / 2 h / Ambient temperature

10: 38percent ammonia / tetrahydrofuran; H₂O / 5 h / Ambient temperature

11: sodium cyanoborohydride, 37percent hydrochloric acid / H₂O; methanol / 1 h / 0 °C

12: 1.) 37percent hydrochloric acid; 2.) triethylamine / 1.) methanol, water, 10 h, room temp.; 2.) CHCl₃, reflux, 5 h

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; ammonium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Jones-reagent; Celite; camphor-10-sulfonic acid; water; sodium cyanoborohydride; triethylamine; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4020(01)80642-6

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (136992-56-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LDA, N,N,N',N'-tetramethylethylenediamine / 1.) THF, hexane, -78 deg C, 1h, then -78 deg C, 30 min; 2.) THF, -78 deg C, 2 h

2: Jones-reagent / acetone / 0.33 h / Ambient temperature

3: water, sodium chloride / dimethylsulfoxide / 2 h / 140 °C

4: 88 percent / methanol / 10 h / Ambient temperature

5: 62 percent / dl-camphorsulfonic acid / methanol / 1 h / Heating

6: 79 percent / n-butyllithium / hexane; diethyl ether / 1 h / -78 °C

7: pyridine, chromium (VI) oxide, celite / CH₂Cl₂ / 1 h / Ambient temperature

8: 1M hydrochloric acid / tetrahydrofuran; H₂O / 2 h / Ambient temperature

9: 38percent ammonia / tetrahydrofuran; H₂O / 5 h / Ambient temperature

10: sodium cyanoborohydride, 37percent hydrochloric acid / H₂O; methanol / 1 h / 0 °C

11: 1.) 37percent hydrochloric acid; 2.) triethylamine / 1.) methanol, water, 10 h, room temp.; 2.) CHCl₃, reflux, 5 h

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; ammonium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Jones-reagent; Celite; camphor-10-sulfonic acid; water; sodium cyanoborohydride; triethylamine; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4020(01)80642-6

Reference yield:

(2-bromo-3-methoxyphenyl)acetonitrile (128828-87-5) → (1S,3S)-3-(4-Benzyloxy-butyl)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (136992-56-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 6M sodium hydroxide / methanol / 12 h / Ambient temperature

2: diethyl ether / 1 h / 0 °C

3: 1.) LDA, N,N,N',N'-tetramethylethylenediamine / 1.) THF, hexane, -78 deg C, 1h, then -78 deg C, 30 min; 2.) THF, -78 deg C, 2 h

4: Jones-reagent / acetone / 0.33 h / Ambient temperature

5: water, sodium chloride / dimethylsulfoxide / 2 h / 140 °C

6: 88 percent / methanol / 10 h / Ambient temperature

7: 62 percent / dl-camphorsulfonic acid / methanol / 1 h / Heating

8: 79 percent / n-butyllithium / hexane; diethyl ether / 1 h / -78 °C

9: pyridine, chromium (VI) oxide, celite / CH₂Cl₂ / 1 h / Ambient temperature

10: 1M hydrochloric acid / tetrahydrofuran; H₂O / 2 h / Ambient temperature

11: 38percent ammonia / tetrahydrofuran; H₂O / 5 h / Ambient temperature

12: sodium cyanoborohydride, 37percent hydrochloric acid / H₂O; methanol / 1 h / 0 °C

13: 1.) 37percent hydrochloric acid; 2.) triethylamine / 1.) methanol, water, 10 h, room temp.; 2.) CHCl₃, reflux, 5 h

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; ammonium hydroxide; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Jones-reagent; Celite; camphor-10-sulfonic acid; water; sodium cyanoborohydride; triethylamine; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4020(01)80642-6

upstream raw materials:

di-tert-butyl dicarbonate

(2-bromo-3-methoxyphenyl)acetic acid

5-benzyloxy-1-pentanal

(2-bromo-3-methoxyphenyl)acetonitrile

Downstream raw materials:

(1S,3S)-3-(4-Benzyloxy-butyl)-1-hydroxymethyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

(1S,3S)-3-(4-Benzyloxy-butyl)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester