(S)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol

white to light yellow crystal powde

The experimental procedure used for this reaction was adapted from literature.General procedure: The experimental procedure was adapted from literature. A solution of TIQ ester 4a-e (2.0 g) was added dropwise to a stirred suspension of LiAlHStep 1 (S)-3-Hydroxymethyl-1, 2, 3, 4-tetrahydroisoquinoline can be prepared from L-phenylalanine in accordance with the method described by S. Yamada and T. Kunieda, Chem. Pharm. Bull., 15, 490, (1967).Step 2: Compound A2 (5.3 g, 16.47 mmol) and (S)-(1, 2, 3, 4-tetrahydroisoquinolin-3- yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reaction mixture was cooled to 0 C and TEA (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixture was then warmed to rt and was stirred overnight. The solution was concentrated and the crude product was purified by silica gel chromatography (EtOAc/hexanes, gradient, 0% to 80%) to obtain compound A3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 mm (8 mm method). Mass observed (ESI): 449.25 (M+H).Compound 62 (5.3 g, 16.47 mmol) and (S)-(1, 2, 3, 4-tetrahydroisoquinolin-3-yl)methanol (2.96 g, 18.12 mmol) were dissolved in dichloromethane (47.1 mL). The reaction mixture was cooled to0 C and triethylamine (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixturewas then warmed to room temperature and was stirred overnight. The solution was concentratedand the crude product was purified by silica gel chromatography (ethyl acetate/hexanes, gradient, 0% to 80%) to obtain compound 12 (7.22 g, 16.10 mmol, 98% yield).Compound 2 (5.3 g, 16.47 mmol) and (S)-(1, 2, 3, 4-tetrahydroisoquinolin-3-yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reactionmixture was cooled to 0 oc and TEA (3.44 mL, 24.71 mmol) was added dropwise underAr. The reaction mixture was then warmed to rt and was stirred overnight. The solutionwas concentrated and the crude product was purified by silica gel chromatography(EtOAc/hexanes, gradient, 0% to 80%) to obtain compound 3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 min (8 min method). Mass observed (ESI+): 449.25 (M+H).

Molecular Weight:163.22
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:163.099714038
Monoisotopic Mass:163.099714038
Topological Polar Surface Area:32.3
Heavy Atom Count:12
Complexity:149
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes