Benzyl 4-Hydroxybenzoate → HCID 86701942, compound

HRID 717929Notes

Reaction equation

HRID 717929 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.O[C:15]1[CH:30]=[CH:29][C:18]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:17][CH:16]=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>O1CCCC1>[CH2:22]([O:21][C:19]([C:18]1[CH:29]=[CH:30][C:15]([O:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)=[CH:16][CH:17]=1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86701942HCID 86701942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (1 g, 5.34 mmol) in tetrahydrofuran (38.1 ml) was added benzyl 4-hydroxybenzoate (1.341 g, 5.87 mmol) and triphenylphpsphine polymer bound (4.45 g, 8.01 mmol). The reaction mixture was cooled to 0° C. and a solution of (E)-diisopropyl diazene-1,2-dicarboxylate (1.367 ml, 6.94 mmol) in tetrahydrofuran (5 mL) was added dropwise over 15 minutes. The reaction was allowed to stir at room temperature for 16 hours and the mixture was filtered. The solids were washed with dichloromethane, and the combined filtrates were concentrated and purified by normal phase chromatography to give the title compound.

Workup

  1. filtrationthe mixture was filtered
  2. washThe solids were washed with dichloromethane
  3. concentrationthe combined filtrates were concentrated
  4. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-598c9083681d42c0bfbd5fbe906ac2ff
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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