Benzylamine → HCID 53801080, compound

HRID 258381Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH:12]=[CH:13][CH3:14]>>[CH2:1]([NH:8][CH2:14][CH2:13][CH:12]=[CH:11][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 53438943HCID 53438943, compound

Product 1

HCID 53801080HCID 53801080, compound

Procedure

Reaction of benzylamine with 5-bromopent-2-ene gives 5-benzylamino-2-pentene, which can be condensed with the half-ester of malonic acid, as described in Section XXVIII. Subsequent diazo transfer and cycloaddition, according to Section XXVIII, provides ethyl 3-benzyloxycarbonyl-7-methyl-2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate. Processing of this compound as in Section XXXVIII provides the desired trisubstituted compound.

Sources & evidence

ORD record: ord-b81f050361cf469b9b485c7d11993d50
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266569

Reaction notes

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