Lithium borohydride → HCID 58564709, compound

HRID 2039976Notes

Reaction equation

HRID 2039976 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:26])=[C:20]([CH:25]=3)[C:21](OC)=[O:22])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[BH4-].[Li+]>O1CCCC1>[OH:22][CH2:21][C:20]1[CH:25]=[C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([CH2:8][N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[CH:28][CH:27]=2)[CH:17]=[CH:18][C:19]=1[CH3:26]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68760189HCID 68760189, compound

Product 1

HCID 58564709HCID 58564709, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reactor is charged with 100 mg (0.26 mmol) of methyl 5-(4-((4-methylpiperazin-1-yl)methyl)benzamido)-2-methylbenzoate (example 82, step 2) in 5 ml anhydrous tetrahydrofuran and 38 mg (1.75 mmol) of lithium borohydride is added. The mixture is stirred at room temperature for 16 hours. The mixture is then concentrated under reduced pressure, taken off into 60 ml of ethyl acetate, washed with 20 ml of a saturated NaHCO3 solution, 20 ml of water and 20 ml of a saturated NaCl solution. The organic phase is dried, evaporated and the residue is taken off and triturated into ethylic ester to give a solid (80 mg, 86%)

Workup

  1. additionis added
  2. concentrationThe mixture is then concentrated under reduced pressure
  3. washwashed with 20 ml of a saturated NaHCO3 solution, 20 ml of water and 20 ml of a saturated NaCl solution
  4. customThe organic phase is dried
  5. customevaporated
  6. customtriturated into ethylic ester

Sources & evidence

ORD record
ord-5d8a872da3034de2888c777df74d19bb
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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