Boron trifluoride etherate → HCID 59701077, compound

HRID 902047Notes

Reaction equation

HRID 902047 reaction equation
[C:1]1([CH2:7][O:8][N:9]=[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].B(F)(F)F.CCOCC>CO>[C:1]1([CH2:7][O:8][NH:9][CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 5003444Sodium cyanoborohydrideHCID 136331936HCID 136331936, compound

Product 1

HCID 59701077HCID 59701077, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.27 g of the compound obtained in stage A are dissolved in 450 ml of methanol. 12.14 g of sodium cyanoborohydride are subsequently added, followed, dropwise at 0° C., by 20.57 g (18.36 ml) of boron trifluoride etherate. After evaporating the methanol, the residue is treated with NaH2PO4 (1M aqueous solution) and then extraction is carried out with a heptane/AcOEt 1:2 mixture. Washing is subsequently carried out with an acidic aqueous solution and then the organic phase is dried with MgSO4 and the solvent is evaporated. The compound is taken up in an ether/pentane mixture at 0° C. The compound crystallizes. 3.81 g of the expected compound (89%) are isolated.

Workup

  1. customAfter evaporating the methanol
  2. additionthe residue is treated with NaH2PO4 (1M aqueous solution)
  3. extractionextraction
  4. washWashing
  5. dry with materialthe organic phase is dried with MgSO4
  6. customthe solvent is evaporated
  7. customis taken up in an ether/pentane mixture at 0° C
  8. customThe compound crystallizes

Sources & evidence

ORD record
ord-04e2175be1e041848c3b127b4c6efa68
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

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