Acetone → HCID 54411918, compound

HRID 965247Notes

Reaction equation

HRID 965247 reaction equation
[NH2:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.C([BH3-])#N.[Na+].[CH3:30][C:31]([CH3:33])=O.C(#N)C>C(Cl)(Cl)Cl.[B].C(O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][C@@H:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:10][C@@H:2]3[NH:1][CH:31]([CH3:33])[CH3:30])=[CH:13][CH:14]=2)=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 70070524HCID 70070524, compound

Product 1

HCID 54411918HCID 54411918, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 5462311BoronSolvent

Procedure

The title compound was prepared in a similar manner to Example 31 from (±) cis-2-amino-1-[4-(4-fluorophenoxy)phenoxy]indane (70 mg, 0.2 mmol), sodium cyanoborohydride (25 mg, 0.4 mmol), acetone (0.29 ml, 4 mmol) and acetonitrile (10 ml). After subjecting the crude product to column chromatography on silica gel eluting with 5% ethanol in chloroform, residual boron impurities were removed by dissolving the product in hexanes and filtering. Removal of the hexanes in vacuo afforded the title compound (40 mg) as a colourless oil.

Workup

  1. customwere removed
  2. dissolutionby dissolving the product in hexanes
  3. filtrationfiltering
  4. customRemoval of the hexanes in vacuo

Sources & evidence

ORD record
ord-f3a91b6abe574ad09e285264dc6cb2dd
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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