Lithium borohydride → HCID 52942013, compound

HRID 1510094Notes

Reaction equation

HRID 1510094 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][N:9]([C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:12])[CH2:8][CH2:7][N:6]1C(OC(C)(C)C)=O)=O.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][CH:5]1[NH:6][CH2:7][CH2:8][N:9]([C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:12])[CH2:10]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66920226HCID 66920226, compound

Product 1

HCID 52942013HCID 52942013, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 1 (100 mg, 0.18 mmol) was dissolved in THF (3.6 ml), lithium borohydride (11.8 mg, 0.54 mmol) was added, and the reaction was stirred at room temperature for 2 h. The mixture was partitioned between a saturated ammonium chloride solution and EA. The organic phase was washed with a saturated sodium hydrogencarbonate solution and water, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in DCM (20 ml), TFA (5 ml) was added, and the mixture was stirred at room temperature for 1 h. The solvents were evaporated and the obtained solid was purified by preparative HPLC. The eluate was lyophilized overnight, the residue dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight. 53 mg of the title compound were obtained in the form of the (3-hydroxymethyl-piperazin-1-yl)-(2-phenoxy-1-phenyl-1H-indol-3-yl)-methanone hydrochloride.

Workup

  1. customThe mixture was partitioned between a saturated ammonium chloride solution and EA
  2. washThe organic phase was washed with a saturated sodium hydrogencarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (20 ml)
  6. additionTFA (5 ml) was added
  7. stirringthe mixture was stirred at room temperature for 1 h
  8. customThe solvents were evaporated
  9. customthe obtained solid was purified by preparative HPLC
  10. waitThe eluate was lyophilized overnight
  11. dissolutionthe residue dissolved in a small quantity of MOH
  12. additionmixed with hydrochloric acid (0.1 M)
  13. waitlyophilized overnight

Sources & evidence

ORD record
ord-1f62261d4c5d46b79305dbc4e98c64a3
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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