Dimethylformamide → HCID 69002069, compound

HRID 1909648Notes

Reaction equation

HRID 1909648 reaction equation
[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[C:26]([O:30][C:31](=[O:34])[CH2:32]Br)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>O>[C:26]([O:30][C:31](=[O:34])[CH2:32][N:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[CH2:13][O:12][C:11]1[CH:19]=[CH:20][C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 16222641HCID 16222641, compound

Product 1

HCID 69002069HCID 69002069, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine (200 mg, 0.658 mmol) was taken into DMF (2 mL), and t-butylbromoacetate (141 mg, 0.724 mmol) was added, followed by potassium carbonate (182 mg, 1.317 mmol). The mixture was heated to 60° C. and left to react overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over sodium sulfate, and concentrated to dryness. The compound was then purified by flash chromatography (eluted with 0.5% methanol in dichloromethane with a 40:1 silica ratio) to obtain the title product (161 mg, 0.423 mmol, 64% yield); LCMS; m/z 381.52, found 381 (M); 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.66-1.73 (m, 2H), 1.79-1.85 (m, 2H), 1.99-2.06 (m, 1H), 2.63-2.69 (m, 1H), 3.18-3.22 (m, 2H), 3.40 (d, J=17.2, 1H), 3.59 (d, J 16.8, 1H), 3.79-3.83 (m, 1H), 3.91-3.95 (m, 2H), 6.82 (d, J 8.88, 2H), 7.08 (d, J8.8, 2H), 7.15-7.27 (m, 5H).

Workup

  1. additionwas added
  2. waitleft
  3. customto react overnight
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe compound was then purified by flash chromatography (
  9. washeluted with 0.5% methanol in dichloromethane with a 40:1 silica ratio)

Sources & evidence

ORD record
ord-ffbc7a00225844009201fe235190cf8c
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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