Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate → HCID 57449676, compound

HRID 2266275Notes

Reaction equation

HRID 2266275 reaction equation
CON(C)[C:4]([CH: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]([CH: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 57449675Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylateHCID 178495008HCID 178495008, compound

Product 1

HCID 57449676HCID 57449676, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of (±)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (1.73 g, 6.4 mmol) in dry THF (40 mL) was cooled in an ice-salt bath and 1.34 M 4-methoxybutylmagnesium chloride in THF (10 mL, 1.34 mmol) was added dropwise over 3 min. The cooling bath was allowed to expire and the mixture was stirred at rt for 6 h, poured into ice cold 3% aq HCl (100 mL) and extracted with ether (2×100 mL). The combined ether extracts were washed with satd aq NaHCO3 (35 mL), dried over MgSO4 and concentrated to afford (±)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate (1.78 g, 93%) as an oil.

Workup

  1. extractionextracted with ether (2×100 mL)
  2. washThe combined ether extracts were washed with satd aq NaHCO3 (35 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dba91ff8eb6d49dba47248856a8681c9
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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