3-(Trifluoromethyl)benzaldehyde → HCID 67443239, compound

HRID 1667223Notes

Reaction equation

HRID 1667223 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:14][C:15]([F:24])([F:25])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][N:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]1

Participants

5

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67443239HCID 67443239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (0.25 g, 1.34 mmol) in dichloromethane (10 mL) was added 3-(trifluoromethyl)benzaldehyde (0.3 g, 1.745 mmol) and sodium triacetoxyborohydride (0.43 g, 2.01 mmol). The mixture was stirred at room temperature for 16 hours. Then the reaction mixture was diluted with dichloromethane and washed with NaHCO3 solution. The organic layer was dried with MgSO4, concentrated, and purified by flash chromatography, eluting with 50% ethyl acetate/hexane to yield the title compound.

Workup

  1. washwashed with NaHCO3 solution
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography
  5. washeluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a2755189f48a4107a2a07ea28744f85a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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