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

HRID 1182662ノート

反応式

HRID 1182662 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-eabe886922f44740a0e2dee11993f525
出典データセット
uspto-grants-2014_03
特許番号
US08664207B2

反応ノート

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