Hydrochloric Acid → HCID 66781309, compound

HRID 1096723Notes

Reaction equation

HRID 1096723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:14][CH:13]2[C:12](=O)[CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:16][NH:17][CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCCl.C([O-])(O)=O.[Na+]>[ClH:1].[CH3:16][N:17]([CH3:18])[CH:12]1[CH2:11][CH2:10][C:9]2([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH:13]1[CH2:14]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66781708HCID 66781708, compound

Product 1

HCID 66781309HCID 66781309, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The mixture of 5-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-2-one (110 mg, 0.45 mmol) in DCE (3 mL) and dimethylamine (2M solution in THF, 5 mL, 4.5 mmol) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol) at room temperature. The reaction mixture was stirred for 0.5 h, then the reaction mixture was diluted with saturated NaHCO3, extracted with CH2Cl2(3×), dried over K2CO3, filtered and concentrated in vacuo to afford the target compound. The oily crude residue (96 mg, 79%) was converted to HCl salt. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.11 (t, 1 H) 1.77-1.87 (m, 1 H) 1.96-2.02 (m, 1 H) 2.03-2.22 (m, 3 H) 2.25-2.37 (m, 1 H) 2.81 (d, 3 H) 2.92 (d, 3 H) 3.72-3.90 (m, 1 H) 6.96 (dd, 7 H) 7.21 (d, 7 H) 7.33 (d, 7 H) 12.07-12.30 (broad, 1 H), 13C NMR (126 MHz, CHLOROFORM-d) δ ppm 15.96 (s, 1 C) 24.22 (s, 1 C) 25.84 (s, 1 C) 31.02 (s, 1 C) 33.20 (s, 1 C) 42.65 (s, 1 C) 42.69 (s, 1 C) 69.75 (s, 1 C) 125.96 (s, 1 C) 128.61 (s, 1 C) 130.52 (s, 1 C) 130.57 (s, 1 C) 132.58 (s, 1C) 142.82 (s, 1 C). 13C NMR (400 MHz, CHLOROFORM-d) d ppm 15.96 (s, 1 C) 24.22 (s, 1 C) 25.84 (s, 1 C) 31.02 (s, 1 C) 33.20 (s, 1 C) 42.65 (s, 1 C) 42.69 (s, 1 C) 69.75 (s, 1 C) 125.96 (s, 1 C) 128.61 (s, 1 C) 130.52 (s, 1 C) 130.57 (s, 1 C) 132.58 (s, 1C) 142.82 (s, 1 C). MS (M+1) 270.

Workup

  1. extractionextracted with CH2Cl2(3×)
  2. dry with materialdried over K2CO3
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford the target compound

Sources & evidence

ORD record
ord-95f1488bec374b459fe3612e5f530ae9
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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