Benzylamine → HCID 22560188, compound

HRID 983406Notes

Reaction equation

HRID 983406 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:16]1[CH2:20][CH2:19][CH:18]([C:21](=O)[CH2:22][F:23])[C:17]1=[O:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:9]([N:16]1[CH2:20][CH2:19][CH:18]([CH:21]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][F:23])[C:17]1=[O:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22560293HCID 22560293, compound

Product 1

HCID 22560188HCID 22560188, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzylamine (3.9 mL, 35.7 mmol) was added to a solution of 1-benzyl-3-(2-fluoro-acetyl)pyrrolidin-2-one (7.00 g, 29.8 mmol, Example 15) in dichloroethane (150 mL). The solution was cooled to 0° C. and sodium triacetoxyborohydride (8.20 g, 38.7 mmol) added. The reaction mixture was warmed to room temperature and stirred overnight, then washed with aqueous sodium bicarbonate solution and brine. The organic layer was then dried over magnesium sulfate, filtered and concentrated. The residue was purified by chromatography (99:1 to 97:3 dichloromethane/methanol) to afford the title compound (7.2 g) as a mixture of diastereomers. MSCI: m/z 327 (MH+).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washwashed with aqueous sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (99:1 to 97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-c6328d1ba33a4fdd83b53fb1bf3f522b
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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