Triphenylphosphine → (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

HRID 1182662Notes

Reaction equation

HRID 1182662 reaction equation
O[C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C:8]1[N:13]([CH3:14])[C:12](=[O:15])[CH:11]=[CH:10][N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH3:14][N:13]1[C:12](=[O:15])[CH:11]=[CH:10][N:9]2[C:8]1=[N:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]12

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 673709162-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

Product 1

HCID 67379018(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-oneYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one (130 mg, 0.62 mmol) in anhydrous THF (2 mL) is added triphenylphosphine (163 mg, 0.62 mmol). Five minutes later, diethyl azodicarboxylate (DEAD, 0.45 mL, 0.93 mmol) in toluene is added dropwise. The mixture is stirred at room temperature for 2 hours. Solvent is removed under vacuum, the residue is treated with 0.02 N HCl (40 mL). The precipitate is filtered off, and the filtrate is washed with CH2Cl2. The aqueous phase is evaporated to dryness under high vacuum to give product as solids (108 mg, yield 92%), which is used for the next reaction without further purification. MS (ESI) m/z 192.1 [M+H]+.

Workup

  1. customSolvent is removed under vacuum
  2. additionthe residue is treated with 0.02 N HCl (40 mL)
  3. filtrationThe precipitate is filtered off
  4. washthe filtrate is washed with CH2Cl2
  5. customThe aqueous phase is evaporated to dryness under high vacuum

Sources & evidence

ORD record
ord-eabe886922f44740a0e2dee11993f525
Source dataset
uspto-grants-2014_03
Patent number
US08664207B2

Reaction notes

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