Sodium borohydride → HCID 67125438, compound

HRID 1470735Notes

Reaction equation

HRID 1470735 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([C:15]2[CH:16]=[CH:17][C:18]([C@@H:21]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH3:22])=[CH:19][CH:20]=2)[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67125425HCID 67125425, compound

Product 1

HCID 67125438HCID 67125438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 13.60 g (32.0 mmol) (S)-1-benzyl-4-[4-(1-propionylamino-ethyl)phenyl]-pyridinium bromide (XXI.1) in 270 mL ethanol are slowly added 2.42 g (64.1 mmol) sodium borohydride at 0° C. The mixture is stirred for 48 h at rt. After that time, the solvent is removed in vacuo and ethyl acetate is added. The mixture is extracted with 1N HCl. The aq. phase is neutralized with 4N NaOH, the precipitate is filtered off and dried at 45° C. to yield the desired product.

Workup

  1. customat 0° C
  2. customAfter that time, the solvent is removed in vacuo and ethyl acetate
  3. additionis added
  4. extractionThe mixture is extracted with 1N HCl
  5. filtrationthe precipitate is filtered off
  6. customdried at 45° C.

Sources & evidence

ORD record
ord-41510126ac014c298a41d1be2acf791b
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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