Triphenylphosphine → HCID 69254250, compound

HRID 902699Notes

Reaction equation

HRID 902699 reaction equation
[Cl:1][C:2]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][OH:9].[N:32]1([C:38]2[CH:39]=[C:40](O)[CH:41]=[CH:42][CH:43]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:6][CH2:7][CH2:8][O:9][C:42]1[CH:41]=[CH:40][CH:39]=[C:38]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[CH:43]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1413433-MorpholinophenolHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Product 1

HCID 69254250HCID 69254250, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A stirring solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propan-1-ol (282 mg, 0.38 mmol) in toluene (25 mL) was treated with 3-morpholin-4-yl-phenol (75 mg, 0.42 mmol). Polymer bound triphenylphosphine (224 mg, 0.67 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture was stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (127 mg, 0.63 mmol) was added in a dropwise fashion. After stirring at room temperature overnight, the crude reaction mixture was filtered and the solid washed with toluene (25 mL). The filtrate was concentrated in vacuo. Purification by preparative HPLC (YMC 75×30 mm, 25 ml/min, 85-100% CH3CN over) led to the isolation of the morpholine product. The free base was treated with 1 M HCl in Et2O (0.1 ml) and the mixture was concentrated in vacuo to afford the title compound as a solid, 104 mg (41%). MS(ES) m/e 609.4 (M+).

Workup

  1. additionwas then added
  2. stirringAfter stirring at room temperature overnight
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe solid washed with toluene (25 mL)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customPurification by preparative HPLC (YMC 75×30 mm, 25 ml/min, 85-100% CH3CN over)
  8. additionThe free base was treated with 1 M HCl in Et2O (0.1 ml)
  9. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-59aae67ef74049879b1cd98fad08dd13
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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