Acetic Acid → HCID 54036921, compound

HRID 52275Notes

Reaction equation

HRID 52275 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C:6]2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([F:12])[C:5]=2[O:4][CH2:3]1.[CH3:15][C:16]([CH3:18])=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[F:12][C:11]1[C:5]2[O:4][CH2:3][C@H:2]([NH:1][CH:16]([CH3:18])[CH3:15])[CH2:7][C:6]=2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 22871215(R)-8-fluoro-5-methoxy-3-aminochroman

Product 1

HCID 54036921HCID 54036921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-Amino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (1.62 g, 8.21 mmol) was dissolved in anhydrous methanol (20 mL) and to this was acetone (6.0 mL, 82.1 mmol) added. The reaction was cooled (ice-bath) then sodium cyanoborohydride (0.92 g, 14.8 mmol) was added, the pH was adjusted to 4-5 with acetic acid and the reaction was allowed to stir at room temperature overnight. The solvent was removed in vacuo, the remains were taken into a 2M solution of NH3 and then extracted thrice with diethyl ether. The combined ether portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue that was used as is in the next reaction. GC-MS (70 eV) M=239 (81%).

Workup

  1. additionadded
  2. temperatureThe reaction was cooled (ice-bath)
  3. customThe solvent was removed in vacuo
  4. extractionextracted thrice with diethyl ether
  5. dry with materialThe combined ether portions were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-39c00d1800c44318a85186ee35c4f668
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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