Triphenylphosphine → 3-(7-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

HRID 2089476Notes

Reaction equation

HRID 2089476 reaction equation
[N:1]1([C:6]2[CH:15]=[C:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH:13]3O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:17]1[CH:21]=[C:20]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[N:19]=[CH:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1>[CH:25]([O:24][C:22]([C:20]1[N:19]([CH:13]2[C:14]3[C:9](=[CH:8][CH:7]=[C:6]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:15]=3)[CH2:10][CH2:11][CH2:12]2)[CH:18]=[N:17][CH:21]=1)=[O:23])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 675492557-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-olHCID 178459416HCID 178459416, compound

Product 1

HCID 591993253-(7-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-ol (0.300 g, 1.382 mmol), and isopropyl 4-imidazolecarboxylate (0.149 g, 0.967 mmol), which can be prepared as described in Example 1, in THF (10 mL) at 0° C. is added triphenylphosphine (0.293 g, 1.382 mmol) and dimethyl azodicarboxylate (40% wt. in toluene, 0.505 g, 1.382 mmol). After 10 minutes, the cooling bath is removed and the mixture is stirred for another 30 minutes. Water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. The resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(7-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 354.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.40 (d, J=6.3 Hz, 3 H), 1.41 (d, J=6.3 Hz, 3 H), 1.66-1.75 (m, 1 H), 1.79-1.87 (m, 1 H), 1.98-2.01 (m, 4 H), 2.13-2.25 (m, 2 H), 2.77 (ddd, J=16.7, 8.8, 5.3 Hz, 1 H), 2.88 (dt, J=16.7, 5.6 Hz, 1H), 3.12-3.24 (m, 4 H), 5.27 (sept, J=6.3 Hz, 1 H), 6.14 (d, J=2.5 Hz, 1 H), 6.24 (t, J=5.1 Hz, 1 H), 6.62 (dd, J=8.6, 2.5 Hz, 1 H), 7.08 (d, J=8.6 Hz, 1 H), 7.31 (s, 1 H), 7.73 (d, J=1.3 Hz, 1 H).

Workup

  1. customcan be prepared
  2. customthe cooling bath is removed
  3. additionWater is added
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures)

Sources & evidence

ORD record
ord-b8dfb51a681a40aa97085d6e17ff942e
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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