Phthalimide → HCID 131729310, compound

HRID 657133Notes

Reaction equation

HRID 657133 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][C@H:7]1[CH2:12][C@@H:11]([CH2:13]O)[CH2:10][N:9]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:8]1)([CH3:4])[CH3:3].[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][C@H:7]1[CH2:12][C@@H:11]([CH2:13][N:31]2[C:27](=[O:37])[C:28]3[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30]2=[O:32])[CH2:10][N:9]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:8]1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 131729309HCID 131729309, compound

Product 1

HCID 131729310HCID 131729310, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To cis-phenylmethyl (3RS,5RS)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-(hydroxymethyl)-1-piperidinecarboxylate (550 mg; 1.4 mmol) in THF (25 ml) was added phthalimide (250 mg; 1.7 mmol), triphenylphosphine (450 mg; 1.7 mmol), and diethyl azodicarboxylate (300 mg; 1.7 mmol). The reaction was allowed to stir at room temperature under N2 for 16 hours. The reaction was partitioned between EtOAc (150 ml) and water (50 ml), the layers were separated, the organic layer was washed with brine and dried with Na2SO4. The solvents were removed and the crude residue was purified by chromatography on silica gel using a 10%-100% EtOAc/hexanes gradient to provide the desired compound (690 mg; 93%) as a yellow oil.

Workup

  1. customThe reaction was partitioned between EtOAc (150 ml) and water (50 ml)
  2. customthe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. customThe solvents were removed
  6. customthe crude residue was purified by chromatography on silica gel using a 10%-100% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-8850f50449094270aee6f3fc8235b362
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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