Benzylamine → HCID 58293278, compound

HRID 1912440Notes

Reaction equation

HRID 1912440 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH:19]=O)[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>O1CCCC1.O>[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH2:19][NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:4]

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 10779491HCID 10779491, compound

Product 1

HCID 58293278HCID 58293278, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-oxopropyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.68 g) in tetrahydrofuran (57 ml) was added benzylamine (6.53 ml) at room temperature, and the mixture was stirred for 1 hour. The mixture was cooled to 0° C., and thereto was added sodium triacetoxyborohydride (5.07 g). The mixture was stirred at room temperature for 12.5 hours. To the reaction mixture were added water (12 ml) and saturated aqueous ammonium chloride solution (200 ml), and the mixture was extracted with n-hexane/ethyl acetate (1/2, 210 ml×2, 120 ml×2) 4 times. To the combined organic layer was added n-hexane (150 ml), and the mixture was extracted with 10% aqueous potassium bisulfate solution (180 ml×3) 3 times. The combined aqueous layer was neutralized by 4M aqueous sodium hydroxide solution to pH 7 to 8, and thereto was added saturated aqueous sodium bicarbonate solution (100 ml). The mixture was extracted with ethyl acetate (200 ml). The separated aqueous layer was extracted with ethyl acetate (200 ml×2) twice, and the combined organic layer was washed with saturated aqueous sodium chloride solution (200 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (7.69 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 12.5 hours
  2. extractionthe mixture was extracted with n-hexane/ethyl acetate (1/2, 210 ml×2, 120 ml×2) 4 times
  3. additionTo the combined organic layer was added n-hexane (150 ml)
  4. extractionthe mixture was extracted with 10% aqueous potassium bisulfate solution (180 ml×3) 3 times
  5. additionwas added saturated aqueous sodium bicarbonate solution (100 ml)
  6. extractionThe mixture was extracted with ethyl acetate (200 ml)
  7. extractionThe separated aqueous layer was extracted with ethyl acetate (200 ml×2) twice
  8. washthe combined organic layer was washed with saturated aqueous sodium chloride solution (200 ml)
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b17a400be17b45c1aa9d9c4d9791692e
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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