Methylamine → HCID 69886259, compound

HRID 1245298Notes

Reaction equation

HRID 1245298 reaction equation
C(O[C:6]([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH:11]2[C:15]([O-:17])=[O:16])[CH:9]1[C:18]([O-:20])=[O:19])=O)(C)(C)C.C[NH2:22]>C1COCC1.[C-]#N.[K+]>[C:15]([CH:11]1[CH:12]([C:13]([NH:8][CH3:6])=[O:14])[CH:10]1[CH:9]([C:18]([OH:20])=[O:19])[NH2:22])([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 21911181HCID 21911181, compound

Product 1

HCID 69886259HCID 69886259, compoundYield 139.8%

Reagents, catalysts & solvents 2

HCID 9032Potassium CyanideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (1SR, 2 SR, 5RS, 6RS) 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate (312 mg, 0.9 mmol) in dry THF (6 mL) under argon was added methylamine (2.74 mL, 5.4 mmol) and potassium cyanide (3 mg, 0.05 mmol). After stirring overnight in an ultrasonic bath, the solvent was removed under reduced pressure. The residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1) to give 272 mg of the desired compound (80% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-670fc464e8bb451298f57863ca37bba0
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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