HCID 59226064, compound → HCID 59226069, compound

HRID 2370275Notes

Reaction equation

HRID 2370275 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:12][CH2:11][C:10](=[N:13][S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH:22]1([Mg]Br)[CH2:24][CH2:23]1>C(OCC)C>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]1[CH2:8][CH2:9][C:10]([NH:13][S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])([CH:22]2[CH2:24][CH2:23]2)[CH2:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 59226064HCID 59226064, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 59226069HCID 59226069, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 3.00 g (9.05 mmol) of 2-methyl-propane-2-sulfinic acid [4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-amide (25) in 15 mL of diethyl ether was added dropwise to 54.3 mL (27.1 mmol) of a 0.5 M solution of cyclopropylmagnesium bromide in diethyl ether precooled to −78° C. The reaction solution was stirred at −78° C. for 1 h and was allowed to warm to room temperature overnight. The reaction was quenched by dropwise addition of saturated aqueous Na2SO4, dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by silica gel chromatography to yield 800 mg of the title compound (26) as diastereomeric mixture. Rt=2.22 min, 2.25 min (Method C). Detected mass: 374.3 (M+H+).

Workup

  1. customprecooled to −78° C
  2. temperatureto warm to room temperature overnight
  3. customThe reaction was quenched by dropwise addition of saturated aqueous Na2SO4
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e9c034714be14d1d82bf7bf95e91674d
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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