Imidazole → Tert-butyl 2-(2-bromoethyl)morpholine-4-carboxylate

HRID 555127Notes

Reaction equation

HRID 555127 reaction equation
O[CH2:2][CH2:3][CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1.N1C=CN=C1.[Br:22]C(Br)(Br)Br>C(Cl)Cl>[Br:22][CH2:2][CH2:3][CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 44182317tert-Butyl 2-(2-hydroxyethyl)morpholine-4-carboxylate

Product 1

HCID 57850090Tert-butyl 2-(2-bromoethyl)morpholine-4-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 mL round-bottomed flask at 0° C. was added tert-butyl 2-(2-hydroxyethyl)morpholine-4-carboxylate (0.176 g, 0.762 mmol), DCM (4 mL), 1H-imidazole (0.104 g, 1.524 mmol), perbromomethane (0.379 g, 1.143 mmol), and triphenylphoshphine (0.190 g, 0.723 mmol). The mixture was stirred overnight slowly reaching room temperature. The yellow solution was further diluted with 50 mL of DCM, washed with water, brine, dried over sodium sulfate, and filtered. The crude product was then pushed through a plug of silica gel and the solvent was removed to give 213 mgs of a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (s, 9H), 1.94 (q, J=6.86 Hz, 1H), 2.56-2.66 (m, 1H), 2.76-2.91 (m, 1H), 3.35-3.47 (m, 4H), 3.50-3.61 (m, 1H), 3.68 (br. s., 1H), 3.74-3.86 (m, 2H).

Workup

  1. customslowly reaching room temperature
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-6c13863345ce49f6b4eeb8b124eb10f9
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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