Methyl morpholine oxide → HCID 71285294, compound

HRID 1481764Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:17]([CH:18]([OH:22])[CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([O:8][C:9]1[C:17]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To activated 4 Å molecular sieves (4.3 g, 250 mg/mmol) was added a solution of 1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-ol obtained above (ca. 17.22 mmol) in DCM (90 mL). The mixture was cooled to 0° C. before NMO (3.00 g, 25.61 mmol) and TPAP (300 mg, 0.85 mmol, 5 mol %) were added subsequently. The reaction was stirred at 0° C. for 15 min and then allowed to warm to room temperature. After 2 h complete conversion of staring material was observed. Molecular sieves were filtered off and were washed with DCM. The mother liquor was concentrated and the residue was purified by column chromatography (EtOAc/hexanes, 5-15% gradient). 1-(4-(Benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-one was obtained as a white solid (4.85 g) in 92% yield over 2 steps.

Workup

additionwere added subsequently
temperatureto warm to room temperature
waitAfter 2 h complete conversion of staring material was observed
filtrationMolecular sieves were filtered off
washwere washed with DCM
concentrationThe mother liquor was concentrated
customthe residue was purified by column chromatography (EtOAc/hexanes, 5-15% gradient)

Sources & evidence

ORD record: ord-2bda49951d77433a965ea2c446378675
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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