Hydrochloric Acid → 12-(Methanesulfonyl)-3-methoxy-5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquinolino[2,1-g][1,6]naphthyridine--hydrogen chloride (1/1)

HRID 476950Notes

Reaction equation

HRID 476950 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:24]=[CH:23][C:22]2[C@H:21]3[N:12]([CH2:13][C@@H:14]4[C@H:19]([CH2:20]3)[N:18]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:17][CH2:16][CH2:15]4)[CH2:11][CH2:10][C:9]=2[CH:8]=1.[ClH:29]>>[ClH:29].[CH3:5][O:6][C:7]1[CH:24]=[CH:23][C:22]2[C@H:21]3[N:12]([CH2:13][C@@H:14]4[C@H:19]([CH2:20]3)[N:18]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:17][CH2:16][CH2:15]4)[CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67870848(8aR,12aS,13aS)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine acetate

Product 1

HCID 16889812-(Methanesulfonyl)-3-methoxy-5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquinolino[2,1-g][1,6]naphthyridine--hydrogen chloride (1/1)

Procedure

(8aR,12aS,13aS)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine acetate (1.0 g) is dissolved in 50 ml 5N aqueous hydrochloric acid, and the solution evaporated to dryness. The product is suspended in ethyl acetate and filtered, air dried and recrystallized from methanol/acetone to yield (8aR,12aS,13aS)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-isoquino[2,1-g][1,6]naphthyridine hydrochloride.

Workup

  1. customthe solution evaporated to dryness
  2. filtrationfiltered
  3. customair dried
  4. customrecrystallized from methanol/acetone

Sources & evidence

ORD record
ord-e03f274aa66a4268ad237d7f215bc9a6
Source dataset
uspto-grants-1989_12
Patent number
US04886798

Reaction notes

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