ChemicalBook CAS DataBase List (R)-N-Boc-1,2,3,4-tetrahydro-3-isoquinolinylmethanol

(R)-N-Boc-1,2,3,4-tetrahydro-3-isoquinolinylmethanol synthesis

5synthesis methods

Product Name:(R)-N-Boc-1,2,3,4-tetrahydro-3-isoquinolinylmethanol
CAS Number:845543-81-9
Molecular formula:C15H21NO3
Molecular Weight:263.33

2,3(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) 3-methyl ester, (3R)-

312639-49-9
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(R)-N-Boc-1,2,3,4-tetrahydro-3-isoquinolinylmethanol

845543-81-9
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Yield:845543-81-9 24%

Reaction Conditions:

with lithium aluminium tetrahydride at 0 - 20; for 18 h;

Steps:

2A.1

To a 0 °C solution of a portion of the above material (2.30 g, 7.90 MMOL) was added LiAIH4 (600 mg, 15.8 MMOL) as a solid in two portions. The reaction was allowed to warm to RT overnight. After 18 H, THE reaction was quenched by slow addition of water (1 ml), followed by aq. NAOH (1.5 ML, 25% w/v), and finally more water (2 MI). The resulting mixture was stirred vigorously for 1 h, then filtered and concentrated. The crude residue was purified by column chromatography (silica, 0-->65% ETOAC/HEXANES) to give the desired product (500 mg, 1.89 mmol, 24%). LCMS (Conditions A): tR = 4.2 min; (M+H) + = 264.

References:

WO2005/14540,2005,A1 Location in patent:Page/Page column 52

24424-99-5 Synthesis