Lithium Chloride → HCID 59302564, compound

HRID 2237440Notes

Reaction equation

HRID 2237440 reaction equation
C([O:3][C:4]([C:6]1[S:20][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[O:21][CH3:22])=O)C.[Li+].[Cl-].[Li+].[BH4-]>C1COCC1>[CH2:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C:8]2[C:7]([O:21][CH3:22])=[C:6]([CH2:4][OH:3])[S:20][C:9]=2[CH2:10][CH2:11]1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4148881Lithium borohydrideHCID 59302561HCID 59302561, compound

Product 1

HCID 59302564HCID 59302564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step c) (2.5 g, 7.8 mmol) was dissolved in 125 mL dry THF and treated with LiCl (0.65 g, 15.3 mmol) followed by LiBH4 (15.3 mL of 2M). After stirring for 1 hour, the reaction was quenched carefully with EtOH and HOAc till no gas evolution was observed. The crude reaction mixture was partitioned between water and DCM. The organic extract was dried over MgSO4 and concentrated to give 2.3 g of a clear oil which was purified by silica chromatography (30% EtOAc/Hex) to give 1.03 g of the subtitle compound.

Workup

  1. customthe reaction was quenched carefully with EtOH and HOAc till no gas evolution
  2. customThe crude reaction mixture
  3. customwas partitioned between water and DCM
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad43e53686cf4b22929a71cbe2cee83d
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

Loading…