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[ CAS No. 510-77-0 ] {[proInfo.proName]}

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Chemical Structure| 510-77-0
Chemical Structure| 510-77-0
Structure of 510-77-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 510-77-0 ]

CAS No. :510-77-0 MDL No. :MFCD08063719
Formula : C17H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QENVUHCAYXAROT-YOEHRIQHSA-N
M.W : 285.34 Pubchem ID :10356588
Synonyms :
Narwedin;(-)-Narwedine;3-Deoxy-3-oxo-galanthamine;Narwedine

Safety of [ 510-77-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 510-77-0 ]

* 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.

  • Upstream synthesis route of [ 510-77-0 ]
  • Downstream synthetic route of [ 510-77-0 ]

[ 510-77-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 510-77-0 ]
  • [ 1953-04-4 ]
YieldReaction ConditionsOperation in experiment
85.4%
Stage #1: With L-Selectride In tetrahydrofuran at -50 - -45℃; for 4 h;
Stage #2: With hydrogen bromide In ethanol; water at 15 - 20℃; for 2 h;
Lithium tri-sec-butyl borohydride (L-selectride), (1molar solution in THF, 360.8mL) was added dropwise to a suspension of (4aS,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one, [(−)-narwedine] 6 (50g, 0.175mol) in THF (1000mL) at −50 to −45°C for 1h after which the reaction mixture was stirred at −50 to −45°C for 3h. The completion of the reaction was monitored by qualitative HPLC analysis. Next, the reaction mixture was quenched by adding aqueous hydrogen peroxide (40percent w/w, 85g, 1mol) and the excess peroxide was destroyed by stirring the reaction with an aqueous sodium sulfite solution. The reaction mixture was concentrated under reduced pressure and the product was extracted into toluene (1250mL). The organic extract was concentrated under reduced pressure at 50–55°C to obtain (−)-galanthamine base as an oily mass, which was dissolved in a mixture of ethanol (200mL) and DM water (50mL). Aqueous hydrobromic acid (48percent w/w, 31.09g, 0.185mol) was then added to the (−)-galanthamine base solution and stirred at 15–20°C for 2h. The product was filtered and dried under vacuum at 50–55°C to obtain (−)-galanthamine 1 as a hydrobromide salt as white crystalline powder (55g, 85.4percent yield). Chromatographic purity: 99.85percent (by HPLC); enantiomeric purity: 100percent (by HPLC); mp: 253°C (dec); [α]25D=−96.5[α]D25=-96.5 (c 0.1, water); IR(KBr) (cm−1): 3561, 3043,3022, 2946, 2922, 2619, 2482, 1625, 1512, 1465, 1439, 1282, 1068; δH (300MHz, DMSO-d6): 1.90 (brs, 1H), 2.04 (dd, J = 15.6, 5.1 Hz, 2H), 2.23 (dd, J = 15.6 Hz, 1H), 2.49 (s, 3H), 2.97 (brs, 2H), 3.34 (m, 1H), 3.76 (s, 3H), 3.82 (brs, 1H), 4.09 (s, 1H), 4.48 (m, 2H), 4.59 (s, 1H), 4.78 (d, J = 14.1 Hz, 1H), 5.87 (dd, J = 6, 3 Hz, 1H), 6.12 (d, J = 9 Hz, 1H), 6.79 and 6.85 (2d, J = 8.4, 8.4 Hz, 2H), 9.82 (2brs, 1H); δC (100MHz, DMSO-d6): 30.9 (2×CH2), 35.1 (CH3), 46.4 (CH2), 55.6 (OCH3), 59.4 (CH2), 86.4 (CH), 111.9 (CH), 120.4, 122.8 (CH), 125.4 (CH), 129.8 (CH), 132.8, 144.8, 146.3; HRMS (ESI+): m/z 288.1608 [M+H]+.
Reference: [1] Organic Process Research and Development, 1999, vol. 3, # 6, p. 425 - 431
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 2, p. 117 - 124
[3] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2087 - 2088
  • 2
  • [ 510-77-0 ]
  • [ 1953-04-4 ]
  • [ 1668-85-5 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With cerium(III) chloride heptahydrate In methanol; dichloromethane at -55 - -50℃; for 0.5 h;
Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at -55 - -50℃; for 2.5 h;
A mixture of (4aS,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzezapin-6-one [(−)-narwedine] 6 (10g, 0.035mol), cerium chloride heptahydrate (13.07g, 0.035mol) in methylene chloride–methanol (1:1 v/v, 300mL) was stirred at −55 to −50°C for 30min after which sodium borohydride (3.33g, 0.088mol) was added in portions at −55 to −50°C over a period of 30min. The reaction mixture was stirred at −55 to −50°C for 2h and the completion of the reaction was monitored by qualitative HPLC analysis. Water (10mL) was then added to the reaction mixture and the temperature was raised to 25–30°C. The reaction mixture was concentrated under reduced pressure and the concentrated mass was stirred with chloroform (100mL). The inorganic residue was removed by filtration. The filtrate was washed with water (60mL) and the organic layer was concentrated under reduced pressure. The crude product was stirred with acetone (50mL) at reflux temperature. The slurry mass was cooled to 25–30°C, filtered and dried at 45–50°C under reduced pressure to yield (−)-epigalanthamine 3 as a white crystalline powder (6.85g, 68percent yield). Chromatographic purity: 96.49percent (by HPLC); enantiomeric purity: 97.71percent (by HPLC); mp: 181–182°C; [α]25D=−229.9[α]D25=-229.9 (c 1, CHCl3); IR (KBr, cm−1): 3151, 3031, 3011, 2945, 2916, 1623, 1508, 1459, 1445, 1436, 1272, 1053; δH (300MHz, CDCl3): 1.61–1.75 (m, 2H), 2.18 and 2.75 (dd, J = 12, 12 Hz, 2H), 2.36 (s, 3H), 3.07 and 3.22 (dd, J = 12.9, 12.1 Hz, 2H), 3.59 and 4.05 (dd, J = 15.3, 15 Hz, 2H), 3.83 (s, 3H), 4.60 (m, 2H), 5.79 (d, J = 10.2 Hz, 1H), 6.05 (d, J = 11.7 Hz, 2H), 6.55 and 6.62 (2d, J = 8.1, 8.1 Hz, 2H); δC (100MHz, CDCl3): 32.3 (2×CH2), 34.1 (CH3), 41.6 (CH2), 48.0, 53.8 (CH2), 55.8 (OCH3), 60.1 (CH2), 62.7 (CH), 88.4 (CH), 110.8 (CH), 121.5, 126.2 (CH), 128.9 (CH), 131.9 (CH), 132.9, 143.8, 146.6; HRMS (ESI+): m/z 288.1614 [M+H]+
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 2, p. 117 - 124
  • 3
  • [ 510-77-0 ]
  • [ 1953-04-4 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 3, p. 406 - 412
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 2, p. 117 - 124
  • 4
  • [ 510-77-0 ]
  • [ 1953-04-4 ]
  • [ 1668-85-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 2, p. 117 - 124
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