Diazald → 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate

HRID 61471

Reaction equation

HRID 61471 reaction equation
[N+](=[CH2:3])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[CH2:18]([N:25]1[CH2:30][C@@H:29]([OH:31])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC>[CH2:18]([N:25]1[CH2:30][C@@H:29]([O:31][CH3:3])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6628DiazaldHCID 9550DiazomethaneHCID 866214902-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

Product 1

HCID 1317319302-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylateYield 3.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diazomethane was generated (from 5 g of Diazald) and distilled together with ether into a mixture of 2-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (0.60 g, 0.0016 mol) and around 1 g of silica gel in 10 mL of ether. After distillation, the mixture was stirred at rt overnight. The mixture was diluted with methylene chloride, filtered to remove silica gel. The filtration was concentrated to dry and the resulting residue was applied on column, eluting with 0 to 40% EtOAc in Hexane, to yield the methyl ether compound (20 mg, 3.2%). MS (ESI): (M+H)+=398.1.

Workup

  1. distillationAfter distillation
  2. additionThe mixture was diluted with methylene chloride
  3. filtrationfiltered
  4. customto remove silica gel
  5. filtrationThe filtration
  6. concentrationwas concentrated
  7. customto dry
  8. washeluting with 0 to 40% EtOAc in Hexane

Sources & evidence

ORD record
ord-d6b50734fdab42abaef84eeb7dbd4c9d
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Linked notes

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