Sodium Carbonate → (R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamide

HRID 880225

反応式

HRID 880225 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-:16].[Na+].[Na+].C([SiH](CC)CC)C.[C]=O>CN(C=O)C>[CH:15]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1)=[O:16]

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 28560458N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamideHCID 178418416HCID 178418416、化合物2 回

生成物 1

HCID 86691231(R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Combine N-[(1R)-1-(4-bromophenyl)ethyl]-methanesulfonamide (10 g, 35 mmol), (1,1′-bis(diphenylphosphino)-ferrocene)palladium(II) chloride (733 mg, 0.9 mmol), sodium carbonate (3.81 g, 35 mmol) and DMF (50 mL) in a 300 mL PARR reactor. Add triethylsilane (11.6 mL, 0.72 mmol) and purge the reactor with carbon monoxide three times. Charge the reactor with carbon monoxide (50 psi) and stir the mixture at 90° C. for 15 h. Cool the reactor to ambient temperature; open; filter mixture through a Celite® pad; and wash the pad with DCM (150 mL). Sequentially wash the filtrate with water then brine (2×80 mL). Concentrate the organic phase under reduced pressure to obtain the residue as an orange oil. Purify the orange oil by silica gel flash chromatography eluting with hexane/EtOAc (0 to 30% EtOAc) to provide the title compound (5.6 g, 70%, ee>98%). MS (m/z): 228 (M+1).

後処理

  1. temperatureCool the reactor to ambient temperature
  2. filtrationfilter mixture through a Celite® pad
  3. washand wash the pad with DCM (150 mL)
  4. washSequentially wash the filtrate with water
  5. concentrationConcentrate the organic phase under reduced pressure

出典と根拠

ORDレコード
ord-e84f96b910b44827b4ff26260fbc4ed5
出典データセット
uspto-grants-2015_03
特許番号
US08993568B2

関連ノート

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