tert-Butyl N-allyl-N-{[allyl(cyclopropylmethyl)amino]carbonyl}glycinate → tert-butyl [3-(cyclopropylmethyl)-2-oxo-2,3,4,7-tetrahydro-1H-1,3-diazepin-1-yl]acetate

HRID 1442870Notes

Reaction equation

[CH2:1]([N:4]([C:13]([N:15]([CH2:20][CH:21]=[CH2:22])[CH2:16][CH:17]1[CH2:19][CH2:18]1)=[O:14])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])C=C>C(Cl)Cl>[CH:17]1([CH2:16][N:15]2[CH2:20][CH:21]=[CH:22][CH2:1][N:4]([CH2:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])[C:13]2=[O:14])[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 40 °C

Procedure

A stirred mixture of tert-butyl N-allyl-N-{[allyl(cyclopropylmethyl)-amino]carbonyl}glycinate from Step B (287 mg, 0.93 mmol) and bis(tricyclohexylphosphine)-benzylidene ruthenium (IV) dichloride (Grubbs' catalyst) (192 mg, 0.23 mmol) in anhydrous CH2Cl2 (90 mL) was heated to 40° C. for 2 h. An additional portion of bis(tricyclohexylphosphine)benzylidene ruthenium (IV) dichloride (80 mg, 0.097 mmol) was added and the reaction mixture was heated to 40° C. for a further 2 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 70:30 to provide the title compound. MS: m/z=225 (M-C4H7).

Workup

temperaturethe reaction mixture was heated to 40° C. for a further 2 h
filtrationThe resulting mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe crude product was purified by silica gel chromatography
washeluting with a gradient of hexane

Sources & evidence

ORD record: ord-7e193d768a254477b29aadd7dee70e9c
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659300B2

Reaction notes

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