Lithium borohydride → HCID 18446927, compound

HRID 1983067Notes

Reaction equation

HRID 1983067 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH:10][CH:11]([CH3:13])[CH3:12])=[O:9])[C:3]=1[NH:14][C:15]([C:17]1[N:21]([C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24](OC)=[O:25])[N:20]=[C:19]([C:32]([F:35])([F:34])[F:33])[CH:18]=1)=[O:16].[BH4-].[Li+]>O1CCCC1>[OH:25][CH2:24][C:23]1[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=1[N:21]1[C:17]([C:15]([NH:14][C:3]2[C:4]([C:8]([NH:10][CH:11]([CH3:12])[CH3:13])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:16])=[CH:18][C:19]([C:32]([F:34])([F:35])[F:33])=[N:20]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 18446933HCID 18446933, compound

Product 1

HCID 18446927HCID 18446927, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step B (240 mg) in tetrahydrofuran (3 mL) was added a solution of lithium borohydride (2 mL, 2 M in tetrahydrofuran). After being stirred at room temperature overnight, the reaction was quenched with water. The reaction mixture was diluted with 1 N aqueous HCl, extracted with ethyl acetate, washed with brine, dried and concentrated to give a white solid. The solid was washed with ethyl ether (3×2 mL) to give the title compound (96 mg), a product of the present invention.

Workup

  1. customthe reaction was quenched with water
  2. additionThe reaction mixture was diluted with 1 N aqueous HCl
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a white solid
  8. washThe solid was washed with ethyl ether (3×2 mL)

Sources & evidence

ORD record
ord-e72983a784504411bdc002b54c48ccc2
Source dataset
uspto-grants-2009_06
Patent number
US07541377B2

Reaction notes

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