Lithium borohydride → HCID 67247264, compound

HRID 2425331Notes

Reaction equation

HRID 2425331 reaction equation
C[O:2][C:3](=O)[C:4]([NH:34][C:35](=[O:37])[CH3:36])([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:17]=2)[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:11]=1)[C:5](OC)=[O:6].[Li+].[BH4-]>C1COCC1>[C:30]([O:29][C:27]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:14]=2)[C:10]([CH2:9][C:4]([NH:34][C:35](=[O:37])[CH3:36])([CH2:3][OH:2])[CH2:5][OH:6])=[CH:11]1)=[O:28])([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67246378HCID 67246378, compound

Product 1

HCID 67247264HCID 67247264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 28 (2.50 g, 4.75 mmol) is added to a solution of LiBH4 (0.525 g, 23.8 mmol) in THF (20 mL) at room temperature under inert atmosphere. The reaction is stirred for 2 days, then quenched with water (5.0 mL) and then extracted with methylene chloride (2 and 25 mL). The combined organic layers are dried over MgSO4 and concentrated in vacuo. The residue is purified using silica gel chromatography with methanol (5%)-methylene chloride (95%) to give compound 29.

Workup

  1. customquenched with water (5.0 mL)
  2. extractionextracted with methylene chloride (2 and 25 mL)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified

Sources & evidence

ORD record
ord-77c0699a9c7847f7acd99a9d60b000ce
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

Loading…