Lithium borohydride → HCID 21480573, compound

HRID 1490161Notes

Reaction equation

HRID 1490161 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+]>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

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 18967734HCID 18967734, compound

Product 1

HCID 21480573HCID 21480573, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3,4,4a,5,6,7,8,8a-octahydro-6-(4-methoxyphenyl)methyl-quinolin-2[1H]-one-3-carboxylate (1 g) (prepared according to Example 6) was mixed with 2M lithium borohydride solution in THF (15 ml) and heated at reflux. After 4 hours the reaction mixture was quenched by addition of water. The reaction mixture was partitioned between water and dichloromethane and the organic layer was washed with 2M HCl, then with saturated sodium carbonate solution, dried (MgSO4) and evaporated. The residue was recrystallised from methanol to give the title compound (0.092 g) mp 193°-200° C.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customAfter 4 hours the reaction mixture was quenched by addition of water
  4. customThe reaction mixture was partitioned between water and dichloromethane
  5. washthe organic layer was washed with 2M HCl
  6. dry with materialwith saturated sodium carbonate solution, dried (MgSO4)
  7. customevaporated
  8. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-bf12075d75dd48069ddd2814a764ec57
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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