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

HRID 1442904노트

반응식

HRID 1442904 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 63651,1-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-05a66c7620304b8990f28d551aea96c9
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659264B2

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