1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-3-Hydroxymethyl-2,3-dihydrobenzo[c]azepin-1-one

HRID 660561Notes

Reaction equation

HRID 660561 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[CH:12][C@@H:13]([NH2:16])[CH2:14][OH:15])C.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(#N)C>[OH:15][CH2:14][C@@H:13]1[NH:16][C:4](=[O:3])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 688421982-((R)-3-Amino-4-hydroxy-but-1-enyl)-benzoic Acid Ethyl Ester

Product 1

HCID 68839278(R)-3-Hydroxymethyl-2,3-dihydrobenzo[c]azepin-1-one

Reagents, catalysts & solvents 1

HCID 21584213Acetonitrile tolueneSolvent

Procedure

To a solution of 2-((R)-3-amino-4-hydroxy-but-1-enyl)-benzoic acid ethyl ester (1.8 g, 7.65 mmol) in 1:1 toluene/acetonitrile (4 mL) is added DBU (1 mL, 6.45 mmol) and stirred at RT for 18 h. The white precipitate is filtered to give the title compound: (M+1)+=190.

Workup

  1. filtrationThe white precipitate is filtered

Sources & evidence

ORD record
ord-4bd67b9fe23a4a6b9803b8f9ee2115ac
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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