Propylamine → HCID 69517313, compound

HRID 854965Notes

Reaction equation

HRID 854965 reaction equation
[CH3:1][C:2]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]([C:16]([F:19])([F:18])[F:17])[O:13]2)=[CH:8][CH:7]=1)([CH3:5])[CH:3]=O.[CH2:25]([NH2:28])[CH2:26][CH3:27].C([BH3-])#N.[Na+]>CO.CC(O)=O.C1COCC1>[CH3:5][C:2]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:12]([C:16]([F:18])([F:17])[F:19])[O:13]2)=[CH:8][CH:7]=1)([CH3:1])[CH2:3][NH:28][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 7852PropylamineHCID 5003444Sodium cyanoborohydrideHCID 86599474HCID 86599474, compound

Product 1

HCID 69517313HCID 69517313, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title product of Example 113 Step 3 (198 mg, 0.579 mmole) in 8 mL of MeOH and 1 mL of HOAc was added n-propylamine (68 mg, 1.2 mmoles), 0.9 mL of 1 M sodium cyanoborohydride in THF, and 1 g of activated 4 Å molecular sieves. The resulting mixture was stirred overnight at room temperature. The mixture was diluted with MeOH, filtered through Celite, concentrated, azeotropically distilled with toluene. Chromatography of the residue over silica gel using 10% MeOH—DCM gave the title compound, 220 mg, as a colorless oil.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-af657ae6dcb24a9abdb7d0a43e66b2f5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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