Triethylamine → HCID 86761235, compound

HRID 2265235Notes

Reaction equation

HRID 2265235 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C@H:8]([OH:19])[C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C@H:8]([O:19][S:30]([CH3:29])(=[O:32])=[O:31])[C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68771119HCID 68771119, compound

Product 1

HCID 86761235HCID 86761235, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,3R)-1-(tert-butyl-dimethyl-silyloxy)-3-(3,4-dichloro-phenyl)-butan-2-ol (4.63 g, 13.2 mmol) in DCM (44 mL) at 0° C. were added Et3N (4.6 mL, 33.0 mmol), DMAP (81.0 mg, 0.7 mmol), and MsCl (2.2 ml, 28.4 mmol). The mixture was stirred overnight at rt. The reaction was quenched with water (100 mL) and extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield an orange oil. The product was purified by flash chromatography (Et2O/hexanes) to afford 4.99 g (88%) of the desired product as a colorless liquid. 1H NMR (400 MHz, CDCl3): 7.39 (d, J=8.3, 1H), 7.35 (d, J=2.1, 1H), 7.12 (dd, J=8.3, 2.1, 1H), 4.72-4.69 (m, 1H), 3.71 (dd, J=11.4, 5.7, 1H), 3.64 (dd, J=11.4, 4.3, 1H), 3.24-3.18 (m, 1H), 2.81 (s, 3H), 1.36 (d, J=7.2, 3H), 0.90 (s, 9H), 0.06 (s, 3H), 0.06 (s, 3H).

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customto yield an orange oil
  6. customThe product was purified by flash chromatography (Et2O/hexanes)

Sources & evidence

ORD record
ord-147bc22e625e41e68d34f81c904a2a9c
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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