Triphenylphosphine → HCID 66653592, compound

HRID 1524259Notes

Reaction equation

HRID 1524259 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:34][O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39](O)[CH:38]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:34][O:35][C:36](=[O:44])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=3)[CH2:3]2)[CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 66653098HCID 66653098, compound

Product 1

HCID 66653592HCID 66653592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

Dissolve 4-((R)-3-hydroxy-pyrrolidin-1-yl)-benzonitrile (188 mg, 1.00 mmol), triphenylphosphine (393 mg, 1.50 mmol) and 3-hydroxy-benzoic acid methyl ester (228 mg, 1.5 mmol) into 10 mL of dry THF under Ar. Cooled to 4° C. Add DEAD (0.26 mL, 1.50 mmol) in a drop-wise fashion. Stir mixture with warming to room temperature overnight. LC-MS analysis indicates the desired intermediate. Concentrate the mixture to dryness. Dissolve residue into CH2Cl2 and apply to a 2 mm SiO2 prep plate. Elute with 50% EtOAc/hexanes to give 113 mg of slightly impure 3-[(S)-1-(4-cyano-phenyl)-pyrrolidin-3-yloxy]-benzoic acid methyl ester.

Workup

  1. temperaturewith warming to room temperature overnight
  2. concentrationConcentrate the mixture to dryness
  3. washElute with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-70c44554f83b4e63bab3c1bb7e2cd30f
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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