Sodium Carbonate → rac-(4aR,8aR)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate

HRID 571970Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:4]1[OH:16].C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1.C([O-])([O-])=O.[Na+].[Na+]>CCC(C)=O>[O:23]=[C:22]1[NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][CH:4]2[O:16]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of rac-(3R*,4R*)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate (3.39 g, 14.72 mmol; prepared according to Tetrahedron (2008), 64, 2456-2464) in MEK (40 mL) heated to 60° C. was added CDI (3.58 g, 22.08 mmol, 1.5 eq). The mixture was stirred for 3 h. Na2CO3 (5% aq., 4 mL) was added. The reaction proceeded at rt for 70 min. The two layers were decanted and the aq. layer was extracted with EA (10 mL). The combined org. layers were washed with brine (8 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (DCM to DCM/MeOH 9:1) to afford the title compound as a white solid (2.59 g).

Workup

waitThe reaction proceeded at rt for 70 min
customThe two layers were decanted
extractionthe aq. layer was extracted with EA (10 mL)
washlayers were washed with brine (8 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by CC (DCM to DCM/MeOH 9:1)

Sources & evidence

ORD record: ord-66a48c60ac6c47f8a75cf4d4c77a06f6
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029368B2

Reaction notes

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