HCID 57791809, compound → HCID 57791812, compound

HRID 1091759Notes

Reaction equation

HRID 1091759 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=O)[CH2:8][O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:3][CH2:2]1>C1COCC1>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 57791809HCID 57791809, compound

Product 1

HCID 57791812HCID 57791812, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl 4-(2-morpholino-2-oxoethoxy)piperidine-1-carboxylate (75) (8.84 g, 26.92 mmol) was dissolved in dry THF (50 mL), to this was added borane-methyl sulfide complex (20.19 mL, 40.38 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 (6.50 g, 77% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.45 (9H, s), 1.54-1.45 (2H, m), 1.84-1.79 (2H, m), 2.90-2.84 (2H, m), 3.16-3.03 (6H, m), 3.79-3.67 (5H, m), 3.97 (2H, t), 4.15-4.10 (2H, m).

Workup

  1. additionto this was added borane-methyl sulfide complex (20.19 mL, 40.38 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-1532af5266514ae0be2b76d755b10545
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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