Hydrochloric Acid → [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride

HRID 1369602Notes

Reaction equation

HRID 1369602 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2].[ClH:27]>C(OCC)(=O)C.C(OCC)C>[ClH:27].[ClH:27].[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9799112[3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

Product 1

HCID 20594298[3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

[3S,4aR,6S,8aR]-Ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate was dissolved in ethyl acetate and excess 1M HCl in diethyl ether was added. The resulting white precipitate was filtered and vacuum dried at 50° C. for 18 hr to give 0.62 g of [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride: MS m/z: 364 (m++1); Analysis calculated for C19H29N3O4.2HCl H2O: C, 50.20; H, 6.89; N, 9.25. Found: C, 50.51; H, 6.86; N, 9.25.

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. customvacuum dried at 50° C. for 18 hr

Sources & evidence

ORD record
ord-0c0876a639a74dbebc00b11d97aa093c
Source dataset
uspto-grants-2003_06
Patent number
US06579886B2

Reaction notes

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