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CAS No. : | 1266238-73-6 | MDL No. : | MFCD18904378 |
Formula : | C12H15NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 221.25 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A suspension of compound 1 (2.001 g, 8.027 mmol) and NaBH4 (762 mg, 20.14 mmol) in THF (32 mL) was stirred at 55C bath as methanol (6.5 mL) was added over 30 min. After 30 min, water (20 mL) was added to the mixture and the solution was concentrated to remove organic solvents. After the resulting mixture was diluted with brine (30 mL), the product was extracted with ether (x 2) and the extracts were washed with brine (x 2), combined, dried (Na2S04), and concentrated. The crude residue 2 was used for the next reaction. MS [M+H]+ = 222.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With dimethylsulfide borane complex; In tetrahydrofuran; at 80℃; for 16h;Inert atmosphere; | Step 6 (R)-(4-benzylmorpholin-3-yl)methanol To a solution of the product from the previous step (24 g, 108.55 mmol) in THF (50 mL) under an atmosphere of N2 was added borane-methyl sulfide complex (1.0 M in THF, 40 mL) and the resulting was heated at 80 C. for 16 h. The mixture was cooled to RT, MeOH (60 mL) was added dropwise and concentrated under reduced pressure. The residue was partitioned between MeOH (40 mL) and 1 N aq. NaOH (40 mL) and the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5-10% EtOAc in hexanes) to afford the title compound (21.8 g, 97% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.37-7.18 (m, 5H), 4.59 (t, J=5.3 Hz, 1H), 4.04 (d, J=13.6 Hz, 1H), 3.79-3.64 (m, 2H), 3.58 (dt, J=11.0, 3.4 Hz, 1H), 3.45-3.35 (m, 3H), 3.27 (d, J=13.6 Hz, 1H), 2.56-2.44 (m, 2H), 2.11 (ddd, J=12.1, 9.1, 3.2 Hz, 1H); MS (ES+)Cl2H17NO2 requires: 207, found: 208 [M+H]+. |