Methanol → Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

HRID 8745

반응식

HRID 8745 반응식
[CH2:1]([C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=C.CSC.C[OH:27]>>[O:27]=[CH:4][CH2:3][CH2:2][CH2:1][C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:8][CH2:7]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 11232181Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

생성물 1

HCID 86597419Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

실험 절차

A solution of methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (29.4 g, 0.0945 mol) from Step B in methanol (1000 mL) was cooled to −78° C. in a dry ice/methanol bath and ozone was bubbled into the solution until a blue color persisted. The excess ozone was removed with a stream of nitrogen and then methyl sulfide (69 mL, 0.95 mol) was added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was then concentrated. The residue was then purified by flash chromatography eluting with 2:1 heptane/ethyl acetate to afford the title compound (23.0 g).

후처리

  1. customozone was bubbled into the solution until a blue color
  2. customThe excess ozone was removed with a stream of nitrogen
  3. customthe cooling bath was removed
  4. concentrationThe reaction mixture was then concentrated
  5. customThe residue was then purified by flash chromatography
  6. washeluting with 2:1 heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-093ff50ed82045c98be5e1147b0de0d3
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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