Triethylamine → HCID 72400693, compound

HRID 1245305Notes

Reaction equation

HRID 1245305 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.Cl.[CH2:22]([O:29][NH2:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C1COCC1.[C-]#N.[K+]>[C:15]([CH:11]1[CH:12]([C:13]([NH:30][O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:14])[CH:10]1[CH:9]([C:18]([OH:20])=[O:19])[NH2:8])([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 21911181HCID 21911181, compound

Product 1

HCID 72400693HCID 72400693, compoundYield 134.2%

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 (150 mg, 0.44 mmol) in dry THF (3 mL) under argon was added O-benzylhydroxylamine hydrochloride (421.5 mg, 2.64 mmol), potassium cyanide (1.43 mg, 0.02 mmol) and triethylamine (0.36 mL, 2.64 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 1.5/1) to give 182 mg of the desired compound (89% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was directly purified by flash chromatography (hexane/ethyl acetate 1.5/1)

Sources & evidence

ORD record
ord-580be4684d64453ca5ff5cf858fde295
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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