HCID 57791776, compound → HCID 57791838, compound

HRID 1091788Notes

Reaction equation

HRID 1091788 reaction equation
O=[C:2]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1>C1COCC1>[N:18]1([CH2:2][CH2:3][O:4][CH:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 1

HCID 57791776HCID 57791776, compound

Product 1

HCID 57791838HCID 57791838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl 4-(2-oxo-2-(pyrrolidin-1-yl)ethoxy)piperidine-1-carboxylate (105)(3.5 g, 11.20 mmol) was dissolved in dry THF (50 mL), to this was added borane-methyl sulfide complex (8.40 mL, 16.81 mmol) and the reaction was stirred at 40° C. for 3 hours then at ambient temperature overnight. The gummy mixture was evaporated and was quenched with 2.0 N sodium carbonate (50 mL), extracted with EtOAc (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired material as a colourless liquid, which was taken through directly to the next stage; 1H NMR (400.132 MHz, CDCl3) δ 1.38-1.58 (m, 9H), 1.73-1.86 (m, 4H), 1.86-1.97 (m, 2H), 2.09-2.21 (m, 2H), 2.79-2.91 (m, 2H), 2.96 (t, 2H), 3.06-3.17 (m, 2H), 3.18-3.27 (m, 2H), 3.49 (septet, 2H), 3.65-3.76 (m, 2H), 3.92 (t, 1H).

Workup

  1. additionto this was added borane-methyl sulfide complex (8.40 mL, 16.81 mmol)
  2. customat ambient temperature
  3. customovernight
  4. customThe gummy mixture was evaporated
  5. customwas quenched with 2.0 N sodium carbonate (50 mL)
  6. extractionextracted with EtOAc (3×75 mL)
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-aa5f7fb174d84a059986322407beef77
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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