Lithium borohydride → HCID 66754357, compound

HRID 641358Notes

Reaction equation

HRID 641358 reaction equation
[CH2:1]1[C:14]2[C:5](=[N:6][C:7]([C:15](OCC)=[O:16])=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>O1CCCC1>[OH:16][CH2:15][C:7]1[N:6]=[C:5]2[C:14](=[C:13]3[C:8]=1[CH:9]=[CH:10][CH:11]=[CH:12]3)[CH2:1][CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66753771HCID 66753771, compound

Product 1

HCID 66754357HCID 66754357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 350 mg of ethyl 1,2,3,4-tetrahydro-phenanthridin-6-yl-carboxylate in 10 ml of tetrahydrofuran is added dropwise within five minutes to a suspension of 37 mg of lithium borohydride in 15 ml of tetrahydrofuran, wherein cooling with an ice bath. Then the ice bath is removed and the reaction mixture is stirred for a further 2.5 hours at ambient temperature. For working up, 2 ml of 1 M citric acid are added to the brown reaction solution wherein cooling with an ice bath. The mixture is stirred with 100 ml of ethyl acetate and 50 ml of water and adjusted to pH 10 with 4 N sodium hydroxide solution. The organic phase is separated off, washed with water, dried over magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with ethyl acetate/petroleum ether (1:4 to 1:1) as eluant.

Workup

  1. temperaturecooling with an ice bath
  2. customThen the ice bath is removed
  3. addition2 ml of 1 M citric acid are added to the brown reaction solution
  4. temperaturewherein cooling with an ice bath
  5. stirringThe mixture is stirred with 100 ml of ethyl acetate and 50 ml of water
  6. customThe organic phase is separated off
  7. washwashed with water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated down
  10. customThe flask residue is chromatographed through a silica gel column with ethyl acetate/petroleum ether (1:4 to 1:1) as eluant

Sources & evidence

ORD record
ord-9d9d893cbdb94d5fa062f8ca776749c9
Source dataset
uspto-grants-2010_04
Patent number
US07696212B2

Reaction notes

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