Hydrochloric Acid → HCID 21480573, compound

HRID 1490164Notes

Reaction equation

HRID 1490164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[CH2:19][CH2:18][CH:17]3[CH:12]([CH2:13][CH:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[NH:16]3)[CH2:11]2)=[CH:5][CH:4]=1.[BH4-].[Li+].Cl>C1COCC1>[OH:22][CH2:21][CH:14]1[CH2:13][CH:12]2[CH:17]([CH2:18][CH2:19][CH:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:11]2)[NH:16][C:15]1=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 18967734HCID 18967734, compound

Product 1

HCID 21480573HCID 21480573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

In a manner analogous to Example 6, but using THF solvent instead of CH2Cl2, ethyl 3,4,4a,5,6,7,8,8a-octahydro-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one-3-carboxylate was prepared as a 60:40 w/w mixture of (±)-(3RS,4aSR,6RS,8aRS) to (±)-(3SR,4aSR,6RS,8aRS) isomers). This product was suspended in THF (20 ml) at 0° C. and an ice cold solution of 1M lithium borohydride in THF (13.1 ml) was added. The mixture was left to stir 51/2 hours at 0° C. and then was added to methanolic hydrogen chloride (120 ml). The acidic solution was left to stand 18 hours and was then evaporated. The residue was dissolved in chloroform and washed with saturated sodium carbonate solution, water and then brine. The organic solution was dried (MgSO4), evaporated and the residual oil was left to stir in hexane containing a small quantity of ethyl acetate for 3 days. The resin obtained was purified by repeated chromatography on a 4 mm "Chromatotron" plate. The early running fractions were combined to give 0.2 g of the title compound. This was recrystallised from ethyl acetate mp 205°-209° C.

Workup

  1. customwas prepared as a 60:40 w/w mixture of (±)-(3RS,4aSR,6RS,8aRS) to (±)-(3SR,4aSR,6RS,8aRS) isomers)
  2. waitThe mixture was left
  3. waitThe acidic solution was left
  4. waitto stand 18 hours
  5. customwas then evaporated
  6. dissolutionThe residue was dissolved in chloroform
  7. washwashed with saturated sodium carbonate solution, water
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated
  10. waitthe residual oil was left
  11. stirringto stir in hexane containing a small quantity of ethyl acetate for 3 days
  12. customThe resin obtained
  13. customwas purified

Sources & evidence

ORD record
ord-5dcba1fbdb694e438c3f1e9efe229291
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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