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CAS No. : | 135097-68-6 | MDL No. : | MFCD14635672 |
Formula : | C17H25NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 307.39 | 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 |
---|---|---|
100% | for 16 h; | Intermediate 111 (19.8 g, 64.4 mmol) was stirred under an atmosphere of hydrogenin the presence of 10percent Pd/C (1.98 g, 1.86 mmol) for 16 h. The catalyst wasremoved by vacuum filtration and the filtrate concentrated at reduced pressure to give 13.98 g (100percent yield) of the title compound as a colourless viscous oil, which crystallised on standing.1H NMR (250 MHz, chloroform-d): 6 [ppm] 3.98 - 3.75 (m, 3H), 3.73 - 3.41 (m, 4H),3.03- 2.83 (m, 1H), 2.82-2.65 (m, 1H), 2.12 (t, J = 5.9 Hz, 1H), 1.45 (5, 9H). |
99% | With hydrogen In ethanol at 20℃; | To a solution of (R)-tert-buty{ 2-(benzyloxymethyl)morpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum, and the residue was purified by flash column chromatography to give (R)-tert-buty\\ 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99 percent) as a clear oil. 1H NMR (400MHz, CDCl3): 3.88 (d, 2 H), 3.82 (br, 1 <n="115"/>H), 3.64 (d, 1 H), 3.56 (m, 3 H), 2.94 (m, 1 H), 2.76 (m, 1 H), 1.90 (br, 1 H), 1.44 (s, 9 H); MS m/z 218 (M+H+). |
99% | With hydrogen In ethanol | Step 3. (R)-tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate To a solution of (R)-tert-butyl 2-(benzyloxymethyl)morpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 atmosphere overnight. After filtration, the solvent was removed under vacuum and the residue was purified by flash column chromatography to give (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99percent) as a clear oil. 1H NMR (400 MHz, CDCl3): δ=3.88 (d, 2H), 3.82 (br, 1H), 3.64 (d, 1H), 3.56 (m, 3H), 2.94 (m, 1H), 2.76 (m, 1H), 1.90 (br, 1H), 1.44 (s, 9H); MS m/z 218 (M+H+). |
99% | With hydrogen In 20 C | To a solution of (K)-tert-butyl 2-(benzyloxymethyl)rnorpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum, and the residue was purified by flash column chromatography to give (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99 percent) as a clear oil. 1H NMR (400MHz, CDCl3): 3.88 (d, 2 H), 3.82 (br, 1 H), 3.64 (d, 1 H), 3.56 (m, 3 H), 2.94 (m, 1 H), 2.76 (m, 1 H), 1.90 (br, 1 H), 1.44 (s, 9 H); MS m/z 218 (M+H*). |
99% | With hydrogen In ethanol at 20℃; | To a solution of (R)-tert-butyl 2-(benzyloxymethyl)morpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum, and the residue was purified by flash column chromatography to give (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99percent) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.88 (d, 2H), 3.82 (br, 1H), 3.64 (d, 1H), 3.56 (m, 3H), 2.94 (m, 1H), 2.76 (m, 1H), 1.90 (br, 1H), 1.44 (s, 9H); MS m/z 218 (M+H+). |
99% | With hydrogen In ethanol at 20℃; | Step 3. (R)-tert-Buty\\ 2-(hydroxymethyl)morpholine-4-carboxylate: To a solution of (R)-tert-buty\\ 2-(benzyloxymethyl)morpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum, and the residue was purified by flash column chromatography to give (R)- tert-butyi 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99 percent) as a clear oil. 1H NMR (400MHz, CDCl3): 3.88 (d, 2 H), 3.82 (br, 1 H), 3.64 (d, 1 H), 3.56 (m, 3 H), 2.94 (m, 1 H), 2.76 (m, 1 H), 1.90 (br, 1 H), 1.44 (s, 9 H); MS m/z 218 (M+H+). |
99% | With hydrogen In methanol at 20℃; | To a solution of (K)-lert-buy\\ 2-(benzyloxymethyl)morpholine-4- carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum and the residue was purified by flash column chromatography to give (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99 percent) as a clear oil. 1H NMR (400MHz, CDCl3): 3.88 (d, 2 H)5 3.82 (br, 1 H)3 3.64 (d, 1 H)3 3.56 (m3 3 H), 2.94 (m, 1 H), 2.76 (m, 1 H), 1.90 (br, 1 H), 1.44 (s3 9 H); MS m/z 218 (M+H+). |
99% | With hydrogen In ethanol at 20℃; | Step 3. (R)-tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate. To a solution of (R)-ter/-butyl 2-(benzyloxymethyl)morpholine-4- carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd-C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum and the residue was purified by flash column chromatography to give (R)-.erf-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99 percent) as a clear oil. 1H NMR (400MHz, CDCl3): 3.88 (d, 2 H), 3.82 (br, 1 H), 3.64 (d, 1 H), 3.56 (m, 3 H), 2.94 (m, 1 H), 2.76 (m, 1 H), 1.90 (br, 1 H), 1.44 (s, 9 H); MS m/z 218 (M+H+). |
92% | With hydrogen In ethanol for 16 h; | Step b) 2R-Hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester The oil (1.80 g) was dissolved in 50 ml ethanol and 100 mg palladium on carbon (10percent) was added. The mixture was hydrogenated at 1 atm H2- EPO <DP n="30"/>pressure for 16 h, filtered through silica/alumina (5 cm and 0.5 cm, respectively) and concentrated in vacuo yielding 1.18 g (92percent) 2R- hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester as a white crystalline solid. |
92% | With hydrogen In ethanol at 20℃; for 16 h; | The oil (1.80 g) was dissolved in 50 ml ethanol and 100 mg palladium on carbon (10percent) was added. The mixture was hydrogenated at 1 atm H2-pressure for 16 h, filtered through silica/alumina (5 cm and 0.5 cm, respectively) and concentrated in vacuo yielding 1.18 g (92percent) 2R-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester as a white crystalline solid. |
59% | With hydrogen In ethanol at 70℃; | (R)-2-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester 1c (1.02 g, 3.32 mmol) and 0.45 g of palladium on activated carbon were added to a reaction flask. The reaction flask was purged with hydrogen for three times. 10 mL of ethanol was added under hydrogen atmosphere. The reaction mixture was stirred overnight at 70°C and monitored by thin layer chromatography until the disappearance of the starting materials. The resulting mixture was purified by silica gel column chromatography to obtain the title compound (R)-2-hydroxymethyl-morpholine-4-carboxylate acid tert-butyl ester 1d (0.428 g, yield 59percent) as a colorless oil. MS m/z (ESI): 240.3 [M+1]. 1H NMR (CDCl3, 400 MHz) δ 3.92-3.88 (m, 3H), 3.7-3.64 (m, 1H), 3.60-3.48 (m, 3H), 2.936 (m, 1H), 2.75 (m, 1H), 2.06 (m, 1H), 1.46 (s, 9H). |
59% | With hydrogen In ethanol at 70℃; | (R)-2-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester 1c (1.02 g, 3.32 mmol) and 0.45 g of palladium on activated carbon were added to a reaction flask. The reaction flask was purged with hydrogen for three times. 10 mL of ethanol was added under hydrogen atmosphere. The reaction mixture was stirred overnight at 70° C. and monitored by thin layer chromatography until the disappearance of the starting materials. The resulting mixture was purified by silica gel column chromatography to obtain the title compound (R)-2-hydroxymethyl-morpholine-4-carboxylate acid tert-butyl ester 1d (0.428 g, yield 59percent) as a colorless oil.MS m/z (ESI): 240.3 [M+1].1H NMR (CDCl3, 400 MHz) δ 3.92-3.88 (m, 3H), 3.7-3.64 (m, 1H), 3.60-3.48 (m, 3H), 2.936 (m, 1H), 2.75 (m, 1H), 2.06 (m, 1H), 1.46 (s, 9H). |