Hydrochloric Acid → HCID 68621445, compound

HRID 1244698Notes

Reaction equation

HRID 1244698 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C@@H:25]([N:26]2[CH2:30][C@@H:29]([CH2:31][F:32])[CH2:28][C:27]2=[O:33])[CH2:24][N:11]2[CH2:12][CH2:13][C:14]3[C:19]([C@@H:10]2[CH2:9]1)=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)([CH3:4])([CH3:3])[CH3:2].N[C@@H]1[C@@H](N2C[C@@H](CF)CC2=O)CN2CCC3C([C@@H]2C1)=CC(OC)=C(OC)C=3.Cl>CC(O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[C@@H:25]([N:26]2[CH2:30][C@H:29]([CH2:31][F:32])[CH2:28][C:27]2=[O:33])[CH2:24][N:11]2[CH2:12][CH2:13][C:14]3[C:19]([C@@H:10]2[CH2:9]1)=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 114175671-(2-Amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-4-(fluoromethyl)pyrrolidin-2-oneHCID 44140173HCID 44140173, compound

Product 1

HCID 68621445HCID 68621445, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

[(S,S,S)-3-((S)-4-Fluoromethyl-2-oxo-pyrrolidin-1-yl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido [2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester (2.40 g, 5.02 mmol) was converted to (S)-1-((S,S,S)-2-amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido [2,1-a]isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one in accordance with the general method of Example 1e. The product was dissolved in 2-propanol (10 mL) and treated with hydrogen chloride (5–6 M in 2-propanol, 37 mL). The suspension formed was stirred for 64 h at r.t., then the precipitate was collected by filtration and dried, to afford the title compound (2.04 g, 91%). White solid, m.p. >300° C.

Workup

  1. customThe suspension formed
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-4cb8e34614ff4a44a6408da84d479945
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

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