Methanol → HCID 67981351, compound

HRID 1400055Notes

Reaction equation

HRID 1400055 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[C:9]2([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:20][CH2:19][CH2:18][C:17]4=O)=[CH:12][CH:11]=3)[CH:5]1[CH2:6][N:7]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8]2.S(C)C.CO>C1COCC1>[CH3:1][O:2][CH2:3][CH:4]1[C:9]2([C:10]3[CH:11]=[CH:12][C:13]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[CH:14][CH:15]=3)[CH:5]1[CH2:6][N:7]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8]2

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 67510086HCID 67510086, compound

Product 1

HCID 67981351HCID 67981351, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 6-(methoxymethyl)-1-(4-(2-oxopyrrolidin-1-yl)phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylate (500 mg, 1.29 mmol) obtained in Step 2 of Example XXXIII, in dry THF (10 mL), was added BH3.Me2S complex (3.23 mL, 6.47 mmol, 2M in THF) at 0° C. under nitrogen atmosphere. The reaction mixture was refluxed for 4 h. After completion of the reaction as confirmed by TLC, methanol (20 mL) was added and the reaction mixture was heated to reflux for 1 h. The solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 3:7 EtOAc:Pet. ether) to afford the title compound (400 mg, 86%) as a viscous oil.

Workup

  1. customat 0° C.
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. customAfter completion of the reaction
  4. additionwas added
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux for 1 h
  7. customThe solvents were removed in vacuo
  8. customto afford the crude compound, which
  9. customwas purified by column chromatography (silica gel, 3:7 EtOAc:Pet. ether)

Sources & evidence

ORD record
ord-0483cb1269f44d2890cb1b754edc7aac
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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