Hydrochloric Acid → (+/-)-trans-2-Diethylaminocarbonyl-6-(2-furylmethyl)-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

HRID 2877

Reaction equation

HRID 2877 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[NH:26][C:9]2[CH2:10][C@@:11]3([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=4)[C@H:16]([CH2:17][C:8]=2[C:7]=1[CH3:27])[CH2:15][NH:14][CH2:13][CH2:12]3)=[O:5])[CH3:2].[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH:35]=O.C([BH3-])#N.[Na+].[ClH:41]>CO.C(O)(=O)C>[ClH:41].[CH2:28]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[NH:26][C:9]2[CH2:10][C@@:11]3([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=4)[C@H:16]([CH2:17][C:8]=2[C:7]=1[CH3:27])[CH2:15][N:14]([CH2:35][C:31]1[O:30][CH:34]=[CH:33][CH:32]=1)[CH2:13][CH2:12]3)=[O:5])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7362Furfural2×HCID 5003444Sodium cyanoborohydride2×HCID 22883692(+/-)-trans-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Product 1

HCID 22883648(+/-)-trans-2-Diethylaminocarbonyl-6-(2-furylmethyl)-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1.3 g (3.3 mmol) of (±)-trans-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline, 0.28 ml (4.95 mmol) of acetic acid, 0.33 ml (3.96 mmol) of 2-furaldehyde were dissolved in 50 ml of MeOH under nitrogen atmosphere. 0.415 g (6.6 mmol) of sodium cyanoborohydride were added and the solution stirred for 15 h. Additional acetic acid (0.1 ml), 2-furaldehyde (0.3 ml) and sodium cyanoborohydride (0.2 g) were added. After two hours of stirring the reaction mixture was cooled to 0° C. and 50 ml of 5N hydrochloric acid were added. The solvent was removed in vacuo, the aqueous solution was extracted with Et2O, the pH was adjusted to 8 with 20% NaOH and then extracted with AcOEt. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was dissolved in acetone/MeOH and the solution brought to acidic pH with HCl/Et2O . The precipitate was filtered, yielding 1.7 g of the title compound. M.p.=105° C. dec.

Workup

  1. stirringAfter two hours of stirring the reaction mixture
  2. customThe solvent was removed in vacuo
  3. extractionthe aqueous solution was extracted with Et2O
  4. extractionextracted with AcOEt
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was removed in vacuo
  7. dissolutionThe crude product was dissolved in acetone/MeOH
  8. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-cd9b39ec611d404d9a8ea9bc73cb12d3
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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