Sodium Carbonate → HCID 66705251, compound

HRID 2108796Notes

Reaction equation

HRID 2108796 reaction equation
[CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:11]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][N:9]([C@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:8]2)=O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Si:14]([O:13][CH2:12][C@@H:11]1[CH2:10][N:9]([C@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:8][C@@H:7]1[CH2:5][NH:4][CH:1]1[CH2:2][CH2:3]1)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 66704803HCID 66704803, compound

Product 1

HCID 66705251HCID 66705251, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(3R,4S)-N-Cyclopropyl-4-(tert-butyldimethylsilyl)oxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide (7.00 g) was dissolved in toluene (70 mL). A borane/dimethyl sulfide complex (2.20 mL) was added and the mixture was refluxed for 5 hours while being stirred. Subsequently, the reaction was allowed to cool to room temperature, followed by addition of a 10% aqueous solution of sodium carbonate (42 mL) and stirring at 100° C. for 1 hour. The toluene layer was separated, washed with water (2×30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=4:1) to give (3S,4S)-4-(tert-butyldimethylsilyl)oxymethyl-3-cyclopropylaminomethyl-1-[(1S)-1-phenylethyl]pyrrolidine as a colorless oil (4.78 g).

Workup

  1. additionA borane/dimethyl sulfide complex (2.20 mL) was added
  2. temperaturethe mixture was refluxed for 5 hours
  3. stirringstirring at 100° C. for 1 hour
  4. customThe toluene layer was separated
  5. washwashed with water (2×30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9cb64fdfedf8405f816c5f5cdf30e2e7
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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