Phthalimide → HCID 18423417, compound

HRID 1282005Notes

Reaction equation

HRID 1282005 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH2:17][CH2:18]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][N:24]2[C:23](=[O:25])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:30])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18423452HCID 18423452, compound

Product 1

HCID 18423417HCID 18423417, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.344 g (1.26 mmol) of 1-t-butoxycarbonyl-4-(3-hydroxypropyloxymethyl)piperidine (Example 17, Step 3), 0.926 g (6.3 mmol) of phthalimide, and 0.661 g (2.52 mmol) of triphenylphosphine in 10 mL of THF at 0° C. was added dropwise 0.4 mL of diethylazodicarboxylate (DEAD). The reaction mixture was allowed to warm to rt and was stirred for 36 h. To the reaction mixture was added 20 mL of ether and it was filtered through a thin pad of celite. The filtrate was washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 2:1) to give 1-t-butoxycarbonyl-4-(3-phthalimidopropyloxymethyl)piperidine. Removal of the BOC protecting group was achieved as described in Example 4, Step 2 to give the title compound.

Workup

  1. filtrationwas filtered through a thin pad of celite
  2. washThe filtrate was washed with sat'd NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-6b6a706a83c24d9894ce36553367e020
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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