Benzylamine → HCID 69885961, compound

HRID 1245297Notes

Reaction equation

HRID 1245297 reaction equation
C(OC([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.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.[C-]#N.[K+]>[C:15]([CH:11]1[CH:12]([C:13]([NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:14])[CH:10]1[CH:9]([C:18]([OH:20])=[O:19])[NH2:8])([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 21911181HCID 21911181, compound

Product 1

HCID 69885961HCID 69885961, compoundYield 117.8%

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 (307 mg, 0.9 mmol) in dry THF (7 mL) under argon was added benzylamine (590 μL, 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 3/1) to give 310 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 3/1)

Sources & evidence

ORD record
ord-eff38a68386146699108920f3c9524e6
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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