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

HRID 8745

Reaction equation

HRID 8745 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-093ff50ed82045c98be5e1147b0de0d3
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Linked notes

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