486-99-7

Upstream product

• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 
• 106647-92-1 (R)-1-((S)-1,2-Bis-ethoxycarbonyloxy-ethyl)-6,7-bis-ethoxycarbonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 101006-67-1 (R)-1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 106647-94-3 (R)-1-((S)-1,2-Dihydroxy-ethyl)-6,7-dihydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 106647-95-4 (R)-1-((S)-1,2-Dihydroxy-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 13326-57-3 ethyl 6,7-dimethoxy-3,4-dihydroisoquinoline-1-carboxylate 
• 1673-81-0 6,7-Dimethoxy-1-hydroxymethylisoquinoline 
• 121720-06-7 2-hydroxymethyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 14165-67-4 N-(3,4-dimethoxyphenethyl)-4-methylbenzenesulfonamide 
• 52210-49-8 1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrogen chloride 
• 88387-98-8 [2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyloxy]-acetic acid ethyl ester 
• 124201-24-7 1-formyl-4,5-dimethoxyphenylacetic acid methyl ester 
• 14022-16-3 (2-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol 

Downstream Products

• 87496-32-0 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide 
• 87496-35-3 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid cyclohexylamide 
• 93598-34-6 (+/-)-N-methylcalycotomine 
• 1308338-95-5 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 1308338-32-0 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 109717-72-8 (-)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 
• 109717-73-9 (S)-3,4-dimethoxyphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl-methanol 
• 6872-27-1 (R)-(+)-xylopinine 
• 98979-80-7 8,9-dimethoxy-3-phenyl-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline 

Relevant academic research and scientific papers

Continuous-flow enzymatic resolution strategy for the acylation of amino alcohols with a remote stereogenic centre: Synthesis of calycotomine enantiomers

Both enantiomers of calycotomine (R)-5 and (S)-5 were prepared through the CAL-B-catalysed asymmetric O-acylation of N-Boc-protected (6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinolin-1-yl)methanol [(±)-3)]. The optimum conditions for the enzymatic resolution were determined under continuous-flow conditions, while the preparative-scale resolution of (±)-3 was performed as a batch reaction with high enantioselectivity (E >200). The resulting amino alcohol (S)-3 and amino ester (R)-4, obtained with high enantiomeric excess (ee = 99%), were transformed into the desired calycotomine (S)-5 and (R)-5 (ee = 99%). A systematic study was carried out in a continuous-flow system on the O-acylation of tetrahydroisoquinoline amino alcohol homologues (±)-1 to (±)-3 containing a remote stereogenic centre.

(S)-(-)-α-Methylbenzylamine as an efficient chiral auxiliary in enantiodivergent synthesis of both enantiomers of N-acetylcalycotomine

(S)-(-)-α-Methylbenzylamine 2 was used as a chiral auxiliary in the enantiodivergent synthesis of simple isoquinoline alkaloids. The prochiral imine moiety in compound 4 was reduced with different reagents, giving diastereomeric amines 5a or 5b, which sub

Iridium-Catalyzed Enantioselective α-C(sp3)-H Borylation of Azacycles

We herein report an iridium-catalyzed enantioselective α-C(sp3)-H borylation of a wide range of azacycles. The combination of an iridium precursor and a chiral bidentate boryl ligand has been shown to effectively differentiate enantiotropic methylene C-H bonds from a single carbon center, affording a variety of synthetically useful azacycles from readily available starting materials with good to excellent enantioselectivities.

Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations

A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields. (Chemical Equation Presented).

A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz-Fritsch-Bobbitt cyclization sequence

A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts.

Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems

Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[5, 4-a]isoquinoline-3-oxides (

A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids

A novel, direct, and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes.

Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α- chloro-α-phenylselenoesters. New synthesis of 1,2,3,4- tetrahydroisoquinoline-1-carboxylates

The reaction of N-sulfonyl-β-phenethylamines with α-chloro-a- phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3, 4- tetrahydroisoquinoline-1-carboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is reported.

Enantioselective synthesis of (S)-calycotomine employing catalytic asymmetric hydrogenation with an iridium(I)-(R)-BINAP-phthalimide complex

An optically active 1-hydroxymethyl-substituted tetrahydroisoquinoline alkaloid, (S)-calycotomine 1, was conveniently synthesized by using catalytic asymmetric hydrogenation of 1-benzyloxymethyl-3,4-dihydro-6,7-dimethoxyisoquinoline 6 with 0.5 mol % of an

Reduction and carboxylation of 1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinLum salts. An easy entry to 1-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline alkaloids

At 25°C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0°C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (±)-Calycotomine and its N-Me derivative were obtained in high yields.