Trifluoroacetic acid → HCID 10405830, compound

HRID 1919699Notes

Reaction equation

HRID 1919699 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13]([CH3:14])=[CH:12][CH2:11][CH2:10][CH:9]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)Cl>[C:6]([N:8]1[C@@H:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:10][CH2:11][CH2:12][C@@H:13]1[CH3:14])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 14892358HCID 14892358, compound

Product 1

HCID 10405830HCID 10405830, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.34 g (3.81 mmol) of 1-(tert-Butoxycarbonyl)-6-methyl-2-n-undecyl-1,2,3,4-tetrahydropyridine in 260 mL of CH2Cl2 was added 1.44 g (22.86 mmol) of sodium cyanoborohydride. After being stirred 15 minutes at room temperature, the heterogeneous solution was cooled to −42° C. and TFA (3.7 mL, 38.10 mmol) was added slowly dropwise. After being stirred for 4 h at −42° C., the cold bath was removed, and the reaction mixture was immediately quenched with 190 mL of a saturated aqueous NaHCO3/THF mixture (50:50). The aqueous phase was extracted with CH2Cl2 (2×40 mL) and the combined organic extracts were washed with water and brine. The organic phase was dried with K2CO3, filtered through Celite, and evaporated to give the crude product. Column chromatography using 5% EtOAc in hexanes gave 0.9 g (67%) of the product as a clear colorless oil. 1H NMR (300 MHz) d 3.97-3.84 (m, 1H), 3.83-3.74 (m, 1H), 1.92-1.28 (m, 8H), 1.46 (s, 9H), 1.25 (br s, 18H), 1.22 (d, 3H), 0.89 (t, 3H); 13C NMR (75 MHz) 155.3 (s), 78.7 (s), 51.6 (s), 46.9 (s), 34.3 (s), 31.7 (s), 29.6 (s), 29.5 (s), 29.3 (s), 28.4 (s), 27.2 (s), 26.8 (s), 23.2 (s), 22.7 (s), 20.8 (s), 14.0 (s), 13.6 (s) ppm. FT-IR (neat) 2924, 2854, 2691, 1468, 1394, 1368, 1178, 1091 cm−1.

Workup

  1. temperaturethe heterogeneous solution was cooled to −42° C.
  2. stirringAfter being stirred for 4 h at −42° C.
  3. customthe cold bath was removed
  4. customthe reaction mixture was immediately quenched with 190 mL of a saturated aqueous NaHCO3/THF mixture (50:50)
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×40 mL)
  6. washthe combined organic extracts were washed with water and brine
  7. dry with materialThe organic phase was dried with K2CO3
  8. filtrationfiltered through Celite
  9. customevaporated
  10. customto give the crude product

Sources & evidence

ORD record
ord-79e84c50d0e948e39667c24240c3858a
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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