(2-Hydroxyphenyl)acetic acid → HCID 69016786, compound

HRID 1782026Notes

Reaction equation

HRID 1782026 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[NH:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([N:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 11970(2-Hydroxyphenyl)acetic acidHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 69016786HCID 69016786, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (2-hydroxyphenyl)acetic acid (304 mg, 2.0 mmol) and N,N′-carbonyldiimidazole (405 mg, 2.5 mmol) in DMF (5 nL) was stirred at room temperature for 45 min. A solution of (3S)-pyrrolidin-3-ol (435 mg, 5.0 mmol) in DMF (1.5 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-3% methanol in dichloromethane) to give the subtitled compound (205 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash chromatography (0-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c4d8fc751a0a4040a1047ec949143d05
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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