HCID 59598472, compound → (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate

HRID 253540Notes

Reaction equation

HRID 253540 reaction equation
CON(C)[C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][Mg]Cl>C1COCC1>[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 59598472HCID 59598472, compoundHCID 178495008HCID 178495008, compound

Product 1

HCID 59598474(R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (1.37 g, 5.0 mmol) in THF (10 mL) at −20° C., there was added (4-methoxybutyl)magnesium chloride in THF (1.47 M, 10.2 mL, 15.0 mmol) dropwise such that the temperature remained below −20° C. After addition, the resulting solution was warmed to rt, and quenched with 1 N aq HCl (10 mL). The organic layer was separated, and the aqueous layer was extracted with ether (3×5 mL). The combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL), and dried over Na2SO4. The solvent was then removed in vacuo to give (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate (1.41 g, 93%), which was used for the next step without purification; MS m/s 324 (M+Na+).

Workup

  1. customremained below −20° C
  2. additionAfter addition
  3. customquenched with 1 N aq HCl (10 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ether (3×5 mL)
  6. washThe combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-36657eaff8514535827fb593f8f22f5b
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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