Benzaldehyde → (R)-(-)-2-Benzylaminoheptane

HRID 2368961Notes

Reaction equation

HRID 2368961 reaction equation
[NH2:1][C@@H:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3].[CH:9](=O)[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+].[OH-].[Na+]>C(Cl)Cl.CC(O)=O>[CH2:9]([NH:1][C@@H:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 6992808(2R)-heptan-2-amine

Product 1

HCID 14923313(R)-(-)-2-Benzylaminoheptane

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A sample of 0.65 mL (4.4 mmol) of (R)-(−)-2-aminoheptane (R-44) 0.44 mL (4.4 mmol) of benzaldehyde and 0.1 mL of HOAc were combined in 40 mL of CH2Cl2 and then cooled to 0° C. To the reaction mixture was added 2.75 mg (13 mmol) of sodium triacetoxyborohydride in one portion, which was stirred under argon at room temperature for 28 hours. The reaction mixture was diluted with 30 mL of CH2Cl2, cooled in an ice bath and 80 mL of 5% NaOH (in water) was added. Fractions were separated, organics (Na2SO4) dried and evaporated to 638 mg (71%) of (R)-15. 1H NMR (CDCl3) δ 0.88 (m, 3H), 1.08 (d, 3H J=6.6 Hz), 1.20-1.39 (m, 6H), 1.41-1.67 (m, 2H), 3.62-3.77 (m, 1H), 3.75 (p, 2H, J=12 Hz), 7.17-7.41 (m, 5H); MS (APCI+) m/z (rel): 206 (100); [α]D=+6.9° (c=1.0, MeOH).

Workup

  1. temperaturecooled in an ice bath
  2. customFractions were separated
  3. dry with materialorganics (Na2SO4) dried
  4. customevaporated to 638 mg (71%) of (R)-15

Sources & evidence

ORD record
ord-128917b049cd455db147ecbf116af33c
Source dataset
uspto-grants-2014_04
Patent number
US08703826B2

Reaction notes

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