Sodium Acetate → HCID 87207588, compound

HRID 1499028Notes

Reaction equation

HRID 1499028 reaction equation
N1C2C(=C([C:10]3[N:11]=[C:12]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:13]4[O:18][C:17]5[N:19]=[CH:20][C:21]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:22][C:16]=5[C:14]=4[N:15]=3)C=CC=2)C=C1.[ClH:33].FC1CCNCC1.CC([O-])=O.[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[BH3-]C#N.[Na+]>CN(C=O)C>[Cl:33][C:10]1[N:11]=[C:12]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:13]2[O:18][C:17]3[N:19]=[CH:20][C:21]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:22][C:16]=3[C:14]=2[N:15]=1

Participants

7

Reactant 5

HCID 517045Sodium AcetateHCID 27591584-Fluoropiperidine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 50992382HCID 50992382, compound

Product 1

HCID 87207588HCID 87207588, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 8 (as per Example H above) (80 mg, 0.25 mmol) in dry DMF (12 mL) was added 4-fluoropiperidine hydrochloride (70 mg, 0.5 mmol) and NaOAc (41 mg, 0.5 mmol) under Ar(g). After 20 minutes NaBH(OAc)3 (106 mg, 0.5 mmol) and NaBH3CN (16 mg, 0.25 mmol) were added and the suspension was stirred for 16 h. The DMF was then removed in vacuo, EtOAc (45 mL) was added along with 50% saturated brine (7 mL), the layers separated, extracted with EtOAc (2×15 mL), dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 1-2% MeOH/CH2Cl2) furnished 9 (58 mg, 0.014 mmol, 57%) as a white solid.

Workup

  1. customThe DMF was then removed in vacuo, EtOAc (45 mL)
  2. additionwas added along with 50% saturated brine (7 mL)
  3. customthe layers separated
  4. extractionextracted with EtOAc (2×15 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica (eluant 1-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0ec2aca2f32342c094d26f533bb2bfb9
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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