HCID 178418573, compound → HCID 178465729, compound

HRID 245993Notes

Reaction equation

HRID 245993 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:12][C@H:11](/[CH:13]=[N:14]/[S:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:21][Mg]Br>C(Cl)Cl>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][C@@H:9]1[CH2:12][C@H:11]([CH:13]([NH:14][S:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH3:21])[CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178455589HCID 178455589, compound

Product 1

HCID 178465729HCID 178465729, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid 1-[cis-3-(tert-butyldimethylsilanyloxy)-cyclobutyl]-meth-(E)-ylideneamide (640 mg, 2.02 mmol) in CH2Cl2 (10 mL) at 0° C. was slowly added methylmagnesium bromide (3.0 M in Et20, 1.14 mL, 3.43 mmol). The reaction mixture was stirred at 0° C. for 1 h then quenched with saturated aqueous NH4Cl, diluted with water and extracted with EtOAc (3×). The combined organics were dried over MgSO4 and concentrated to provide 685 mg of 2-methyl-propane-2-sulfinic acid {1-[cis-3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-ethyl}-amide as an off-white waxy solid which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ (ppm) 4.05-4.18 (m, 1H), 3.16-3.31 (m, 1H), 2.85 (d, J=7.2 Hz, 1H), 2.21-2.44 (m, 2H), 1.59-1.76 (m, 3H), 1.20 (s, 9H), 1.18 (d, J=6.0 Hz, 3H), 0.88 (s, 9H), 0.03 (s, 6H).

Workup

  1. customat 0° C.
  2. customthen quenched with saturated aqueous NH4Cl
  3. additiondiluted with water
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e30e3230d96045b8afb77ade5bae119e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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