Hydrochloric Acid → (-)-(4aR,10aR)-3,4,4a,5,10,10a-hexahydro-6-methoxy-4-methyl-9-methylthio-2H-naphth[2,3-b]-1,4-oxazine hydrochloride

HRID 542178Notes

Reaction equation

HRID 542178 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[C:14]2[C:4]=1[CH2:5][C@H:6]1[N:11]([CH3:12])[CH2:10][CH2:9][O:8][C@@H:7]1[CH2:13]2.[ClH:20]>CC(C)=O>[ClH:20].[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[C:14]2[C:4]=1[CH2:5][C@H:6]1[N:11]([CH3:12])[CH2:10][CH2:9][O:8][C@@H:7]1[CH2:13]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 128503Sdz nvi-085

Product 1

HCID 69567089(-)-(4aR,10aR)-3,4,4a,5,10,10a-hexahydro-6-methoxy-4-methyl-9-methylthio-2H-naphth[2,3-b]-1,4-oxazine hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.40 g (5.0 mM) of (-)-(4aR,10aR)-3,4,4a,5,10,10a-hexahydro-6-methoxy-4-methyl-9-methylthio-2H-naphth[2,3-b]-1,4-oxazine are dissolved in 50 ml of acetone and cooled to 0°. 2.75 ml (5.5 mM) of 2N ethereal hydrochloric acid are subsequently added whilst stirring. The precipitated salt is filtered off and washed with ether. (-)-(4aR,10aR)-3,4,4a,5,10,10a-hexahydro-6-methoxy-4-methyl-9-methylthio-2H-naphth[2,3-b]-1,4-oxazine hydrochloride is obtained (m.p. 237°-239°). Recrystallisation from acetone/ether, with the rotation value [α]D20 =-117.4° [c=0.52; methylene chloride/methanol (1:1)].

Workup

  1. temperaturecooled to 0°
  2. filtrationThe precipitated salt is filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-88707eb28e5e4c78925a2d887e64379a
Source dataset
uspto-grants-1987_04
Patent number
US04656167

Reaction notes

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