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

HRID 8745

反応式

HRID 8745 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-093ff50ed82045c98be5e1147b0de0d3
出典データセット
uspto-grants-2006_08
特許番号
US07091211B2

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