9-Fluorenylmethyl chloroformate → 4-(9H-fluoren-9-ylmethyl) 3-methyl 3,4-morpholinedicarboxylate

HRID 1487029Notes

Reaction equation

HRID 1487029 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].C(=O)(O)[O-].[Na+].[C:17](Cl)([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18]>O1CCOCC1.O>[N:2]1([C:17]([O:19][CH2:20][CH:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28]3[C:33]2=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:18])[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 42614243Methyl morpholine-3-carboxylate hydrochloride

Product 1

HCID 733066324-(9H-fluoren-9-ylmethyl) 3-methyl 3,4-morpholinedicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of methyl morpholine-3-carboxylate hydrochloride (2.0 g, 11.01 mmol) in a mixture of 1,4-dioxane (10 mL) and water (20 mL) was added sodium bicarbonate (2.79 g, 33.2 mmol). The suspension was cooled in an ice-water bath and a solution of Fmoc chloride (2.93 g, 11.33 mmol) in 1,4-dioxane (30 mL) was added. The mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between ethyl acetate (150 mL) and water (150 mL). The phases were separated and the organic extract washed with 1 M aqueous HCl (150 mL) and brine (50 mL). The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to leave a colourless gum, 4.2 g. LCMS [LCMS4] Rt 3.10 min, m/z (ES+) 368 (M+H).

Workup

  1. temperatureThe suspension was cooled in an ice-water bath
  2. customThe mixture was partitioned between ethyl acetate (150 mL) and water (150 mL)
  3. customThe phases were separated
  4. extractionthe organic extract
  5. washwashed with 1 M aqueous HCl (150 mL) and brine (50 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customto leave a colourless gum, 4.2 g

Sources & evidence

ORD record
ord-4a1d41170634400abff7bd4bbd66bcfd
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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