Diethyl Ether → HCID 86726795, compound

HRID 1499571Notes

Reaction equation

HRID 1499571 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[C:14](=[O:18])[C@H:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Mg]Br.CCOCC>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[C:14]([OH:18])([CH3:27])[C@H:13]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86726796HCID 86726796, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86726795HCID 86726795, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl-(3R,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-oxopiperidine-1-carboxylate (1.61 g, 4.44 mmol) in THF (30 mL) at −78° C. a solution of methylmagnesium bromide in ether (3.0 M, 4.4 mL, 13 mmol) was added. The reaction was then quenched by adding aq. NH4Cl, and the resulting mixture was extracted with EtOAc. The combined organic extracts were dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 20-80% EtOAc in hexanes to give a mixture of the two diastereoisomers of the sub-title compound as a colorless oil (0.95 g, 56%). LCMS calc. for C20H30N2NaO5 (M+Na)+ m/z=401.2. found 401.0.40% of unreacted starting material was also isolated.

Workup

  1. customThe reaction was then quenched
  2. additionby adding aq. NH4Cl
  3. extractionthe resulting mixture was extracted with EtOAc
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 20-80% EtOAc in hexanes
  8. customto give

Sources & evidence

ORD record
ord-ad46d2f1b1334d058150132687d67dc3
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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