Benzaldehyde → HCID 16735294, compound

HRID 2368962Notes

Reaction equation

HRID 2368962 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 2734517(S)-(+)-2-AminoheptaneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 16735294HCID 16735294, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A sample of 0.15 mL (1 mmol) of (S)-(+)-2-aminoheptane ((S)-44) 0.1 mL (1 mmol) of benzaldehyde and 0.1 mL of HOAc were combined in 10 mL of CH2Cl2 and cooled to 0° C., then added 650 mg (3 mmol) of sodium triacetoxyborohydride in one portion. The reaction mixture was stirred under argon at room temperature for 28 hours. The mixture was diluted with 10 mL of dichloromethane, cooled in an ice bath and 20 mL of 5% NaOH (in water) was added. Fractions were separated, organics were dried (Na2SO4) and evaporated to 154 mg (70%). 1H NMR (CDCl3) 600.88 (m, 3H), 1.08 (d, 3H J=6.6 Hz), 1.19-1.37 (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=+7.8° (c=1.0, MeOH).

Workup

  1. temperaturecooled in an ice bath
  2. customFractions were separated
  3. dry with materialorganics were dried (Na2SO4)
  4. customevaporated to 154 mg (70%)

Sources & evidence

ORD record
ord-15557eb6c5a84037bbea83103df225bc
Source dataset
uspto-grants-2014_04
Patent number
US08703826B2

Reaction notes

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