Dichloromethane → HCID 86590533, compound

HRID 1958457Notes

Reaction equation

HRID 1958457 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11].C(Cl)Cl.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>O>[CH3:22][S:23]([O:11][C@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:2]1[NH:1][S:23]([CH3:22])(=[O:25])=[O:24])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 86590533HCID 86590533, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(1R,2S)-1-amino-2-indanol (300 mg, 2.01 mmol) is in suspended 10 mL DCM, combined with triethylamine (1.68 mL, 12.1 mmol) and cooled to 0° C. Then methanesulphonic acid chloride (467 μL, 6.03 mmol) is added dropwise and the reaction mixture is left to warm up to RT. The reaction mixture is stirred for 1 h at RT and once the reaction is complete it is mixed with water and extracted with DCM. The organic phase is dried on MgSO4, filtered, the filtrate is evaporated down and the crude product B-1a (HPLC-MS: tRet.=1.03 min; MS (m-H)−=304) is used in the subsequent reactions without further purification.

Workup

  1. waitthe reaction mixture is left
  2. temperatureto warm up to RT
  3. extractionextracted with DCM
  4. customThe organic phase is dried on MgSO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated down
  7. custom(HPLC-MS: tRet.=1.03 min; MS (m-H)−=304) is used in the subsequent reactions without further purification

Sources & evidence

ORD record
ord-7d7fad5ef04947ad8d0bc07be3c4abf5
Source dataset
uspto-grants-2013_04
Patent number
US08410126B2

Reaction notes

Loading…