Acetic Acid → HCID 58065382, compound

HRID 1398067Notes

Reaction equation

HRID 1398067 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[C:19]=1[NH2:20])([CH3:17])[CH3:16].[CH3:28][C:29]([CH3:31])=O.C(O)(=O)C>ClCCCl>[CH:29]([NH:20][C:19]1[C:18]([CH:15]([CH3:17])[CH3:16])=[CH:24][CH:23]=[CH:22][C:21]=1[CH:25]([CH3:27])[CH3:26])([CH3:31])[CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 32484DiisopropylanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58065382HCID 58065382, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (3.2 g, 15 mmol) was added into a solution of 2,6-diisopropylaniline (0.940 mL, 4.98 mmol), acetone (1.8 mL, 25 mmol) and acetic acid (0.57 mL, 10 mmol) in 1,2-dichloroethane (30 mL) at room temperature. After stirring at room temperature for 16 h, the reaction was quenched by adding 1M NaOH aq. solution (20 mL). The organic layer was extracted with CH2Cl2 (30 mL), and the volatiles were evaporated under reduced pressure. Column chromatography (silica gel, 20:1 hexane/ethyl acetate) gave the product (0.733 g, 66.8%). 1H NMR (300 MHz, CDCl3) δ 7.24-6.95 (m, 3H), 3.47-3.12 (m, 3H), 2.86 (br. s, 1H), 1.27 (d, J=7.0 Hz, 12H), 1.19 (d, J=6.4 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 142.4, 142.1, 123.6, 123.3, 51.6, 28.0, 24.5, 23.7. HRMS-ESI (m/z): [M+H]+ calcd for C15H26N, 220.2065; found, 220.2064.

Workup

  1. customthe reaction was quenched
  2. additionby adding 1M NaOH aq. solution (20 mL)
  3. extractionThe organic layer was extracted with CH2Cl2 (30 mL)
  4. customthe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-6e03fba26dbe4e5ebbb3041a777e6530
Source dataset
uspto-grants-2014_12
Patent number
US08901336B2

Reaction notes

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