Tert-Butanesulfinamide → 1-O-tert-butyl 4-O-methyl 4-[(2E)-2-tert-butylsulfinyliminoethyl]piperidine-1,4-dicarboxylate

HRID 1442904ノート

反応式

HRID 1442904 の反応式
O=[CH:2][CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:22]([S:25](/[N:27]=[CH:2]/[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:26])([CH3:24])([CH3:23])[CH3:21]

参加物

5

反応物 2

HCID 3382465Tert-ButanesulfinamideHCID 589286301-Tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

生成物 1

HCID 595551491-O-tert-butyl 4-O-methyl 4-[(2E)-2-tert-butylsulfinyliminoethyl]piperidine-1,4-dicarboxylate収率 80.4%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 63651,1-Dichloroethane溶媒

実験手順

A solution of 1-tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate (822 mg, 2.88 mmol), copper(II) sulfate (1.38 g, 8.64 mmol) and 2-methyl-2-propanesulfinamide (354 mg, 3.17 mmol) in dichloroethane (15 mL) was heated at 65° C. for 24 h. The reaction was cooled, filtered and concentrated. The residue was partitioned between saturated aqueous NaHCO3 and dichloromethane, separated, the organic layer dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 7% methanol:dichloromethane to give the title compound (0.9 g). MS: m/z=389.2 (M+1).

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was partitioned between saturated aqueous NaHCO3 and dichloromethane
  5. customseparated
  6. dry with materialthe organic layer dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of 0 to 7% methanol

出典と根拠

ORDレコード
ord-05a66c7620304b8990f28d551aea96c9
出典データセット
uspto-grants-2010_02
特許番号
US07659264B2

反応ノート

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