(S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL

Base Information

• Chemical Name: (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL
• CAS No.: 101467-40-7
• Molecular Formula: C11H15 N O2
• Molecular Weight: 193.24
• Mol file: 101467-40-7.mol

Synonyms:6-Isoquinolinol,1,2,3,4-tetrahydro-7-methoxy-1-methyl-, (R)-; (+)-Salsoline; (R)-Salsoline;d-Salsoline

Chemical Property of (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL

Chemical Property:

• Vapor Pressure: 5.65E-05mmHg at 25°C
• Melting Point: 221°
• Refractive Index: 1.542
• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 157.4°C
• PSA: 41.49000
• Density: 1.106g/cm³
• LogP: 1.93630

Purity/Quality:

98%min ^*data from raw suppliers

SALSOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A further isoquinoline alkaloid which occurs in Salsola Richteri, the base is obtained in the form of a microcrystalline powder which is readily soluble in CHC13 or EtOH but only sparingly so in C6H6 or H20. The alkaloid is soluble in aqueous alkalies but insoluble in petroleum ether. The hydrochloride crystallizes as the sesquihydrate in colourless needles, m.p. 14l-152°C. The N-benzoyl derivative has m.p. 172-4° and the O,N-dibenzoyl compound, m.p. 166-8°C. Treatment with CH2N2 gives Salsolidine (q.v.). The structure, 1:2:3:4-tetrahydro6-hydroxy-7-methoxy-l-methylisoquinoline has been confirmed by synthesis.
• Uses: Salsoline (cas# 89-31-6) was identified as an analyte component in Tibetan Medicine via HPLC-Q-TOF/MS.

Technology Process of (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL

There total 20 articles about (S)-7-METHOXY-1-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL 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: 100.0%

benzyl (6-benzyloxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinoline)-2-carboxylate (350586-92-4) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

With formic acid; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 30h; under 760 Torr;

Reference yield: 89.0%

(+/-)-6-benzyloxy-1,2,3,4-tetrahydro-7-methoxy-1-methylisoquinoline (51745-26-7,123438-47-1) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 0.666667h;

Reference yield:

6-benzyloxy-7-methoxy-1-methyl-3,4-dihydroisoquinoline (6857-58-5) → rac-salsoline (89-31-6,20405-58-7,76419-97-1,101467-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaBH₄ / ethanol / 3 h / 0 °C

2: 89 percent / H₂ / 10percent Pd-C / ethanol / 0.67 h / 20 °C

With sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In ethanol;

upstream raw materials:

rac-salsoline

benzyl (6-benzyloxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinoline)-2-carboxylate

3-methoxy-4-(phenylmethoxy)benzaldehyde

3-benzyloxy-4-methoxy-β-nitrostyrene

Downstream raw materials:

salsoline

6-methyl-8-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

rac-bernumicine

Refernces

• 1、 Pinet,Chavant,Averbuch-Pouchot,Vallee. "Total synthesis of bernumicine and bernumidine, two alkaloids from Berberis nummularia". . p. 65 - 67. Retrieved 2007/10/03.
• 2、 Fujii, Tozo,Yamada, Koichiro,Minami, Shinzaburo,Yoshifuji, Shigeyuki,Ohba, Masashi. "Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine: Syntheses of (+/-)- and (+)-Alangicines". . p. 2583 - 2592. Retrieved 2007/10/02.