Hydrochloric Acid → HCID 11651444, compound

HRID 1408919Notes

Reaction equation

HRID 1408919 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][CH2:5][CH2:4]/[C:3]/1=[N:7]\[C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9].[BH4-].[Na+].Cl>C(O)C>[CH3:16][C:2]1([CH3:1])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C@@H:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178461842HCID 178461842, compound

Product 1

HCID 11651444HCID 11651444, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

(R,E)-N-(2,2-dimethylcyclopentylidene)-1-phenylethanamine (4.61 g, 21.4 mmol) in ethanol (50 mL) was cooled to −78° C. and sodium borohydride (0.41 g, 10.7 mmol) was added and the resulting mixture was allowed to stir at −78° C. for 2 h. At this time, the mixture was slowly treated with 6 N aq HCl (15 mL) followed by warming to rt with vigorous stirring. The organics were removed under vacuum and the remaining aqueous portion was cooled and made basic by addition of 10% aq sodium carbonate and the mixture was then extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine, dried over anhyd. sodium sulfate and the organic was decanted and concentrated on rotovap to yield a yellow liquid as the crude product. This material was purified by flash chromatography on silica gel using ethyl acetate/hexanes mixture as the eluent to afford 3.50 g (75%) of the title compound as a clear oil. HPLC (condition B): retention time=1.90 min. LCMS (condition E): m/z 218+ve. 1H NMR (400 MHz, MeOD) δ 7.29-7.41 (4 H, m), 7.20-7.29 (1 H, m), 3.90 (1 H, q, J=6.60 Hz), 2.59 (1 H, dd, J=9.46, 7.92 Hz), 1.66-1.81 (1 H, m), 1.51-1.67 (1 H, m), 1.38-1.50 (3 H, m), 1.37 (3 H, d, J=6.60 Hz), 1.24-1.36 (1 H, m), 1.05 (3 H, s), 0.92 (3 H, s).

Workup

  1. temperatureby warming to rt with vigorous stirring
  2. customThe organics were removed under vacuum
  3. temperaturethe remaining aqueous portion was cooled
  4. additionmade basic by addition of 10% aq sodium carbonate
  5. extractionthe mixture was then extracted with ethyl acetate (3×100 mL)
  6. washThe combined extracts were washed with brine
  7. customdried over anhyd
  8. customsodium sulfate and the organic was decanted
  9. concentrationconcentrated on rotovap
  10. customto yield a yellow liquid as the crude product
  11. customThis material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3341ec0e6e294326bf00029d5a103bce
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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