Methanol → HCID 49855065, compound

HRID 1400056Notes

Reaction equation

HRID 1400056 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=O)=[CH:15][CH:14]=3)([CH:7]2[CH2:10][O:11][CH3:12])[CH2:5]1)(=O)[CH3:2].B(F)(F)F.CCOCC.S(C)C.CO>C1COCC1>[CH2:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)([CH:7]2[CH2:10][O:11][CH3:12])[CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 67508523HCID 67508523, compound

Product 1

HCID 49855065HCID 49855065, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-(3-acetyl-6-(methoxymethyl)-3-aza-bicyclo[3.1.0]hexan-1-yl)phenyl)pyrrolidin-2-one (360 mg, 1.097 mmol) obtained in Step 1 of Example XXXIV, in dry THF (10 mL), was added BF3.OEt2 (0.027 mL, 0.21 mmol) at 40° C. The reaction mixture was heated at the same temperature for 20 min followed by the addition of BH3.Me2S (2.79 mL, 5.48 mmol, 2M solution). Reaction mixture was heated to reflux for 6 h. After the completion of the reaction as confirmed by TLC, methanol (15 mL) was added to the cold solution and refluxed further for 1 h. The solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 1:9 MeOH:DCM) to afford pure title compound (150 mg, 45%).

Workup

  1. temperatureThe reaction mixture was heated at the same temperature for 20 min
  2. additionfollowed by the addition of BH3
  3. customReaction mixture
  4. temperaturewas heated
  5. temperatureto reflux for 6 h
  6. customAfter the completion of the reaction
  7. additionwas added to the cold solution
  8. temperaturerefluxed further for 1 h
  9. customThe solvents were removed in vacuo
  10. customto afford the crude compound, which
  11. customwas purified by column chromatography (silica gel, 1:9 MeOH:DCM)

Sources & evidence

ORD record
ord-e63218df957b4f1bbf9ac5e4aec6d454
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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