Lithium borohydride → HCID 25269405, compound

HRID 1971255Notes

Reaction equation

HRID 1971255 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:27])[NH:15][CH2:16][C:17]34[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]5)[CH2:18]3)[CH2:24]4)[N:9]2[CH:28]=1)C.[Li+].[BH4-]>C1COCC1>[C:17]12([CH2:16][NH:15][C:14]([C:10]3[N:9]4[CH:28]=[C:6]([CH2:5][CH2:4][OH:3])[N:7]=[C:8]4[CH:13]=[CH:12][CH:11]=3)=[O:27])[CH2:24][CH:23]3[CH2:25][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH2:26]1)[CH2:18]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 25269403HCID 25269403, compound

Product 1

HCID 25269405HCID 25269405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {5-[(adamantan-1-ylmethyl)-carbamoyl]-imidazo[1,2-a]pyridin-2-yl}-acetic acid ethyl ester (65 mg, 0.16 mmol) in THF (5 mL) at RT, is added portion-wise LiBH4 (10 mg, 0.46 mmol). The resulting mixture is stirred at RT for 16 h. The reaction is quenched by the slow addition of water, followed by the addition of EtOAc. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by PTLC (10% MeOH in DCM) the title compound.

Workup

  1. customThe reaction is quenched by the slow addition of water
  2. additionfollowed by the addition of EtOAc
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is back extracted with EtOAc
  5. washThe combined organic layers are washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the residue by PTLC (10% MeOH in DCM) the title compound

Sources & evidence

ORD record
ord-5d889f316b174595a6f67b804dbe6012
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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