1,2-Dichloroethane → HCID 178455057, compound

HRID 585660Notes

Reaction equation

HRID 585660 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCCl.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>CN(C)C1C=CN=CC=1.O.ClCCl>[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][S:42]([CH3:41])(=[O:44])=[O:43])[CH2:27][CH2:28]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178455052HCID 178455052, compound

Product 1

HCID 178455057HCID 178455057, compoundYield 109.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylamine (248 mg, 0.57 mmol) and 1,2-dichloroethane (25 ml). To the stirred solution was added triethylamine (191 μl, 1.37 mmol) followed by methanesulfonyl chloride (53 μl, 0.68 mmol) and three crystals of 4-dimethylaminopyridine. The resulting solution was stirred at room temperature for 18 hr and then poured into a separating funnel containing dichloromethane (100 ml) and water (20 ml). The layers were separated and the aqueous phase extracted with dichloromethane (1×50 ml). The combined organic phases were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo affording the title compound as a pale yellow oil (320 mg, 100%). δH(CDCl3) 0.02 (6H, s), 0.05 (6H, s), 0.78 (9H, s), 0.82 (9H, s), 1.22 (4H, m), 1.70 (2H, m), 1.99 (2H, m), 2.61 (1H, m), 2.81 (3H, s), 3.19 (1H, m), 3.92 (1H, d), 6.13 (1H, d), 6.22 (1H, dd), 6.66 (1H, d).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. additionpoured into a separating funnel
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with dichloromethane (1×50 ml)
  5. washThe combined organic phases were washed with brine (50 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e2ce08b177e4f85a69a83124bf59020
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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