Sodium borohydride → HCID 21064711, compound

HRID 1243780Notes

Reaction equation

HRID 1243780 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21064712HCID 21064712, compound

Product 1

HCID 21064711HCID 21064711, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(2-tert-Butoxycarbonylamino-acetyl)-nicotinic acid methyl ester (132.7 mg, 0.451 mmol) was dissolved into 3 mL of MeOH. To this was added sodium borohydride (18.96 mg, 0.50 mmol) in one portion. After 0.5 h, the reaction mixture was concentrated on a rotary evaporator. The residue was dissolved into 20 mL of EtOAc. The organic phase was washed with 2×20 mL NH4Cl and 1×20 mL of brine, dried (MgSO4) filtered and concentrated to give 133 mg, 99.5% of 6-(2-tert-butoxycarbonylamino-1-hydroxy-ethyl)-nicotinic acid methyl ester.

Workup

  1. concentrationthe reaction mixture was concentrated on a rotary evaporator
  2. dissolutionThe residue was dissolved into 20 mL of EtOAc
  3. washThe organic phase was washed with 2×20 mL NH4Cl and 1×20 mL of brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d4818735b744cb68167d936f55ff984
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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