Dimethylamine → HCID 58173145, compound

HRID 1517523Notes

Reaction equation

HRID 1517523 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@@H:8]2O)=[CH:4][CH:3]=1.C[CH2:13][N:14](CC)[CH2:15]C.CS(Cl)(=O)=O.CNC>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[N:14]([CH3:15])[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7057061HCID 7057061, compound

Product 1

HCID 58173145HCID 58173145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of (S)-6-bromo-indan-1-ol (1 mmol) and NEt3 (4 mmol) in dry THF (5 mL) was stirred at −15° C. under argon. A solution of methanesulfonyl chloride (2 mmol) in dry THF (1 mL) was cooled to −78° C. and then added slowly to the alcohol solution maintaining the temperature below 0° C. The reaction mixture was stirred for 2 h at −15° C. and then purged with dimethylamine gas (12 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. Then, it was filtered to remove salts and solvent was evaporated. Crude was used in next step without further purification.

Workup

  1. temperaturemaintaining the temperature below 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. filtrationThen, it was filtered
  5. customto remove salts and solvent
  6. customwas evaporated
  7. customCrude was used in next step without further purification

Sources & evidence

ORD record
ord-fbaea8e6eaed409a8f58c12370829989
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

Loading…