tert-butyl (S)-1-oxo-1-((R)-2-vinylpiperidin-1-yl)pent-4-en-2-ylcarbamate → tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate

HRID 529526Notes

Reaction equation

[O:1]=[C:2]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[CH:21]=[CH2:22])[C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4]C=C>ClCCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[O:1]=[C:2]1[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[CH:21]=[CH:22][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of tert-butyl (S)-1-oxo-1-((R)-2-vinylpiperidin-1-yl)pent-4-en-2-ylcarbamate (1.00 gm, 3.24 mmol) in DCE (350 mL) was purged with argon for 10 min. Grubbs II catalyst (0.124 gm, 0.146 mmol) was added and the reaction mixture was heated at 60° C. under argon for 18 hr. The reaction mixture was concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate (653 mg, 2.33 mmol, 71.8% yield) as a solid. Anal. Calcd. for C15H24N2O3 m/z 280.3. found: 281.0 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated
customThe crude product was purified
washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record: ord-63e378498cec422da723d5eb1f71aef8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

Loading…