Lithium borohydride → HCID 25269402, compound

HRID 1971247Notes

Reaction equation

HRID 1971247 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([C:24](OCC)=[O:25])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Li+].[BH4-]>C1COCC1>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24][OH:25])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 24808505HCID 24808505, compound

Product 1

HCID 25269402HCID 25269402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-[(adamantan-1-ylmethyl)carbamoyl]imidazo[1,2-a]pyridine-2-carboxylate (7.0 g, 18.35 mmol) in THF (100 mL) at RT, is added portion-wise LiBH4 (799 mg, 36.7 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. The yellow solid is purified by re-crystallization from DCM to give 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. customThe yellow solid is purified by re-crystallization from DCM

Sources & evidence

ORD record
ord-478337a85d3f41a092e3523792924270
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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