Sodium cyanoborohydride → HCID 136050675, compound

HRID 412290Notes

Reaction equation

HRID 412290 reaction equation
Cl.[NH2:2][C:3]1[N:10]=[C:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[C:7]([CH:26]2[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]2)[C:4]=1[CH:5]=O.[BH3-]C#N.[Na+]>CO>[NH2:2][C:3]1[N:10]=[C:9]([C:11]2[C:12]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][CH:14]=[CH:15][C:16]=2[OH:17])[CH:8]=[C:7]2[C:4]=1[CH2:5][N:28]1[CH2:27][CH:26]2[CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 135550596HCID 135550596, compound

Product 1

HCID 136050675HCID 136050675, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of 2-amino-6-[2-(benzyloxy)-6-hydroxyphenyl]-4-(3-piperidinyl)nicotinaldehyde hydrochloride (0.100 g, 0.227 mmol) in methanol was added NaBH3CN (0.040 mL, 0.682 mmol) under an argon atmosphere. The mixture was stirred at room temperature for 12 hrs and concentrated under reduced pressure. The residue was extracted with ethyl acetate and water. The separated organic phase was washed with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 2-(6-amino-5,9-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-yl)-3-(benzyloxy)phenol as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate and water
  3. washThe separated organic phase was washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-bb5faa8d56f74583ae4c3f4ac2a39164
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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