Methyl morpholine oxide → HCID 69064365, compound

HRID 1295090Notes

Reaction equation

HRID 1295090 reaction equation
[CH:1]1([CH2:4][CH:5]2[CH:10]3[CH:6]2[CH2:7][CH2:8][CH:9]3[OH:11])[CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:1]1([CH2:4][CH:5]2[CH:10]3[CH:6]2[CH2:7][CH2:8][C:9]3=[O:11])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69060564HCID 69060564, compound

Product 1

HCID 69064365HCID 69064365, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-cyclopropylmethyl-bicyclo[3.1.0]hexan-2-ol (220 mg, 1.45 mmol) in 10 mL DCM was added sequentially 4 A Molecular sieves (200 mg), NMO (N-Methyl morpholine N-oxide) (339 mg, 2.90 mmol), TPAP label (25.448 mg, 0.0725 mmol). The mixture was stirred overnight at room temperature and plugged through silica gel (3:1 DCM: Et2O) to give 6-cyclopropylmethyl-bicyclo[3.1.0]hexan-2-one as a clear oil; 1H NMR (400 MHz, CDCl3): δ 2.32–2.21 (m, 2H), 2.16 (dd, 1H, J1=13.4 Hz, J2=5.4 Hz), 1.97–1.86 (m, 3H), 1.61–1.53 (m, 1H), 1.38–1.28 (m, 2H), 0.82–0.73 (m, 1H), 0.49–0.44 (m, 2H), 0.09–0.05 (m, 2H).

Sources & evidence

ORD record
ord-7414d95263ca455baa25b5242f670880
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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