3-Fluoro-4-(trifluoromethyl)benzaldehyde → HCID 45274410, compound

HRID 1667274Notes

Reaction equation

HRID 1667274 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:28])[CH2:7][N:8]2[CH2:12][CH2:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:9]2=[O:27])[CH2:2]1.[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[C:38]([F:41])([F:40])[F:39])[CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:11][CH2:12][N:8]([CH2:7][C:6]([NH:5][CH:3]3[CH2:4][N:1]([CH2:33][C:32]4[CH:35]=[CH:36][C:37]([C:38]([F:39])([F:40])[F:41])=[C:30]([F:29])[CH:31]=4)[CH2:2]3)=[O:28])[C:9]2=[O:27])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 53391428HCID 53391428, compound

Product 1

HCID 45274410HCID 45274410, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-azetidin-3-yl-2-[3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl]acetamide (0.083 g, 0.215 mmol; Example 239A) in dichloromethane (5 mL) was added 3-fluoro-4-(trifluoromethyl)benzaldehyde (0.062 g, 0.323 mmol), sodium triacetoxyborohydride (0.088 g, 0.323 mmol) and a few drops of acetic acid. The reaction mixture was stirred at ambient temperature for 16 hours. The mixture was then diluted with dichloromethane and washed with saturated aqueous NaHCO3 solution. The separated organic layer was dried over MgSO4, concentrated, and purified by silica gel flash chromatography eluting with 5-10% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.54 (t, J=7.6 Hz, 1H), 7.28-7.33 (m, 4H), 7.12-7.16 (m, 2H), 6.98-7.05 (m, 4H), 6.30-6.37 (m, 1H), 4.40-4.59 (m, 1H), 3.99 (s, 2H), 3.54-3.66 (m, 4H), 3.50 (t, J=6.5 Hz, 2H), 2.77 (t, J=6.4 Hz, 4H); MS (ESI+) m/z 562 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by silica gel flash chromatography
  5. washeluting with 5-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-5ce951c2ffa24cbba71eea8d0b157808
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…