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

Base Information

• Chemical Name: (1S,3S)-3-(4-Benzyloxy-butyl)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• CAS No.: 128828-97-7
• Molecular Formula: C₂₉H₄₁NO₆
• Molecular Weight: 499.648
• Mol file: 128828-97-7.mol

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

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

There total 20 articles about (1S,3S)-3-(4-Benzyloxy-butyl)-8-methoxy-1-methoxymethoxymethyl-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: 93.0%

chloromethyl methyl ether (107-30-2) + (1S,3S)-3-(4-Benzyloxy-butyl)-1-hydroxymethyl-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-96-6) → (1S,3S)-3-(4-Benzyloxy-butyl)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-97-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)70714-3

Reference yield:

(2-bromo-3-methoxyphenyl)acetic acid (54639-89-3) → (1S,3S)-3-(4-Benzyloxy-butyl)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-97-7)

Guidance literature:

Multi-step reaction with 15 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

13: sodium periodate / H₂O; methanol / 5 h / Ambient temperature

14: sodium borohydride / H₂O; methanol / 0.5 h / Ambient temperature

15: 90 percent / N,N-diisopropylethylamine / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Jones-reagent; Celite; camphor-10-sulfonic acid; water; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; 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)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-97-7)

Guidance literature:

Multi-step reaction with 14 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

12: sodium periodate / H₂O; methanol / 5 h / Ambient temperature

13: sodium borohydride / H₂O; methanol / 0.5 h / Ambient temperature

14: 90 percent / N,N-diisopropylethylamine / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Jones-reagent; Celite; camphor-10-sulfonic acid; water; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; 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:

chloromethyl methyl ether

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

(2-bromo-3-methoxyphenyl)acetic acid

5-benzyloxy-1-pentanal