Sodium triacetoxyborohydride → HCID 86754785, compound

HRID 1602655Notes

Reaction equation

HRID 1602655 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:22])[CH2:6][C@@H:7]([C:20]#[CH:21])[N:8](N1[C@H](C)C[C@H](N)C1=O)[C:9](=[O:11])[CH3:10])[CH3:3].N1C2NCCCC=2C=CC=1C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:2]([O:4][C:5](=[O:22])[CH2:6][C@@H:7]([C:20]#[CH:21])[NH:8][C:9](=[O:11])[CH3:10])[CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehydeHCID 86754788HCID 86754788, compound

Product 1

HCID 86754785HCID 86754785, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 13-11 (450 mg, 1.39 mmol) and 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carbaldehyde (225 mg, 1.39 mmol) in dichloroethane at 0° C. was added Na(OAc)3BH. After 1.5 h the reaction was quenched with sat. NaHCO3, diluted with EtOAc, washed with sat. NaHCO3, brine and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH to give 13-12 as a colorless foam.

Workup

  1. customAfter 1.5 h the reaction was quenched with sat. NaHCO3
  2. additiondiluted with EtOAc
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customremoval of the solvent
  6. customthe residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH

Sources & evidence

ORD record
ord-3ba8fec7416e455cbf3aa04144206153
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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