Ammonia → HCID 57804248, compound

HRID 2103325Notes

Reaction equation

HRID 2103325 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][C@@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:8]1.[NH3:27]>CO>[O:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][C@@H:9]2[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][CH2:4][C:3]([NH2:27])=[O:2])[CH2:8]2)=[CH:14][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69003415HCID 69003415, compound

Product 1

HCID 57804248HCID 57804248, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

4-[(R)-3-(4-Phenoxy-phenoxy)-pyrrolidin-1-yl]-butyric acid methyl ester (200 mg, 0.563 mmol) was taken into 7N Ammonia in methanol solution (5 mL) in a pressure tube. The tube was sealed and heated to 100° C. with stirring and left to react for 48 h. The reaction was concentrated to dryness, and purified by flash silica chromatography (20:1 silica ratio, eluted with a gradient of 10% methanol in dichloromethane to 15% methanol in dichloromethane) to provide the title product (141 mg, 74%); LCMS; m/z 341 (M+1); 1H NMR (400 MHz, DMSO) δ 1.62-1.68 (m, 2H), 1.75-1.78 (m, 1H), 2.06-2.10 (m, 2H), 2.22-2.25 (m, 1H), 2.35-2.43 (m, 3H), 2.59-2.68 (m, 2H), 2.80-2.84 (m, 1H), 4.80-4.83 (m, 1H), 6.69 (s, 1H), 6.89-6.93 (m, 4H), 6.94-6.98 (m, 2H), 7.05-7.09 (m, 1H), 7.24 (s, 1H), 7.32-7.36 (m, 2H).

Workup

  1. customThe tube was sealed
  2. waitleft
  3. customto react for 48 h
  4. concentrationThe reaction was concentrated to dryness
  5. custompurified by flash silica chromatography (20:1 silica ratio
  6. washeluted with a gradient of 10% methanol in dichloromethane to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e21e49317bee4fb4a0ff2c343d6757c8
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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