(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate → (R)-1-Boc-3-acetyl-piperidine

HRID 451713Notes

Reaction equation

HRID 451713 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][Mg]Cl>C1COCC1>[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)(=[O:5])[CH3:20]

Participants

4

Reactant 2

HCID 30025965(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 51922046(R)-1-Boc-3-acetyl-piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (3.320 g, 12.2 mmol) in THF (30 mL) was added 15 mL of 3.0 M MeMgCl in THF at −15° C. under N2. After 0.5 h, the mixture was allowed to warm to rt for 4 h. The reaction mixture was then quenched with 40 mL of 1 NHCl and extracted with ethyl acetate (3×), dried over Na2SO4. After the solvent was evaporated under reduced pressure, the crude (R)-tert-butyl 3-acetylpiperidine-1-carboxylate was directly used in the next step without further purification. MS ESI +ve m/z 250 (M+Na).

Workup

  1. customThe reaction mixture was then quenched with 40 mL of 1 NHCl
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe crude (R)-tert-butyl 3-acetylpiperidine-1-carboxylate was directly used in the next step without further purification

Sources & evidence

ORD record
ord-978c66af53354589ac34b2c3822f311c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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