1,2-Dichloroethane → HCID 24759087, compound

HRID 1672388Notes

Reaction equation

HRID 1672388 reaction equation
[CH:1]1([NH:7][C:8]([CH:10]2[CH2:16][C:13]3([CH2:15][CH2:14]3)[CH2:12][NH:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCCl.[CH:21](=O)[CH:22]([CH3:24])[CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:1]1([NH:7][C:8]([CH:10]2[CH2:16][C:13]3([CH2:14][CH2:15]3)[CH2:12][N:11]2[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67355797HCID 67355797, compound

Product 1

HCID 24759087HCID 24759087, compound

Procedure

To a solution of N-cyclohexyl-5-azaspiro[2.4]heptane-6-carboxamide (10.0 mg, 0.0000450 mol) in 1,2-dichloroethane (0.5 mL, 0.006 mol) was added isobutyraldehyde (4.9 μL, 0.000054 mol), TEA (10 μL, 0.00009 mol), and sodium triacetoxyborohydride (20 mg, 0.00009 mol). After stirring for 30 min. at RT, the reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, then dried (MgSO4), filtered and concentrated in vacuo. The concentrate was purified by prep.-LC/MS to afford the desired product. LC/MS: 279.3 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was purified by prep.-LC/MS

Sources & evidence

ORD record
ord-81f1d31e8c184a769a8b0081374c9d02
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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