1,2-Dichloroethane → HCID 24789154, compound

HRID 1096708Notes

Reaction equation

HRID 1096708 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[C:10](=O)[CH2:9][CH2:8]3)=[CH:3][CH:2]=1.[CH3:15][NH:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:32]CCCl>>[ClH:32].[CH3:15][N:16]([CH3:17])[CH:10]1[CH2:9][CH2:8][C:7]2([C:4]3[CH:5]=[CH:6][C:1]([CH3:14])=[CH:2][CH:3]=3)[CH:11]1[CH2:12]2

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59779113HCID 59779113, compound

Product 1

HCID 24789154HCID 24789154, compound

Procedure

The mixture of 5-p-tolyl-bicyclo[3.1.0]hexan-2-one (100 mg, 0.535 mmol) in DCE (3 mL) and dimethylamine (2M solution in THF, 6 mL, 5.3 mmol) was treated with sodium triacetoxyborohydride (113 mg, 0.53 mmol) at room temperature. The reaction mixture was stirred for 5 h, then the reaction mixture was concentrated, diluted with saturated NaHCO3, extracted with CH2Cl2 (3×), dried over K2CO3, filtered and concentrated in vacuo. The oily crude residue was converted to HCl salt (124 mg, 91.7%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.16 (t, 1 H) 1.73-1.80 (m, 1 H) 1.90-1.95 (m, 1 H) 2.01-2.21 (m, 3 H) 2.33-2.38 (m, 1 H) 2.81 (d, 2 H) 2.91 (d, 3 H) 3.70-3.84 (m, 1 H) 7.01-7.13 (m, 4 H). 13C NMR (400 MHz, CHLOROFORM-d) d ppm 15.70 (s, 1 C) 21.20 (s, 1 C) 24.79 (s, 1 C) 25.82 (s, 1 C) 31.66 (s, 1 C) 33.81 (s, 1 C) 43.55 (s, 1 C) 43.69 (s, 1 C) 70.51 (s, 1 C) 126.70 (s, 2C) 129.38 (s, 2C) 136.31 (s, 1C) 139.58 (s, 1 C). MS (M+1) 216.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with saturated NaHCO3
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89da54dde2b14842b011492a1a3da10d
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

Loading…