Phthalimide → N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide

HRID 602121Notes

Reaction equation

HRID 602121 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][N:40]2[C:39](=[O:41])[C:38]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]3[C:36]2=[O:46])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23521554Tert-butyl 3-(hydroxymethyl)azepane-1-carboxylate

Product 1

HCID 58992706N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimideYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(tert-Butoxycarbonyl)perhydroazepin-3-yl methanol (1.13 g, 4.93 mmol) was dissolved in tetrahydrofuran (10 mL). To this solution, triphenylphosphine (1.60 g, 5.92 mmol) and phthalimide (871 mg, 5.92 mmol) were added and the mixture was stirred at room temperature for 5 min. A 40% toluene solution of diethyl azodicarboxylate (3.23 mL, 7.40 mmol) was then added and the mixture was stirred at room temperature for 4 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.27 g (72%) of the desired compound as a colorless powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed with brine
  4. dry with materialwas dried over magnesium sulfate
  5. customfollowed by evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

Sources & evidence

ORD record
ord-5a699c5b9dd144ba9de0c8e26f7334a9
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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