Methyl morpholine oxide → HCID 57765673, compound

HRID 2357719Notes

Reaction equation

HRID 2357719 reaction equation
C[N+]1([O-])CCOCC1.[CH3:9][C:10]([C@@H:14]1[C@:22]2([CH3:23])[C@H:17]([C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15]1)([CH3:13])[CH2:11][CH3:12]>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:13][C:10]([C@@H:14]1[C@:22]2([CH3:23])[C@H:17]([C:18](=[O:24])[CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15]1)([CH3:9])[CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 54757222HCID 54757222, compound

Product 1

HCID 57765673HCID 57765673, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent3×

Procedure

The solution of NMO (7.2 mg) and molecular sieves 4 Å (41 mg) in methylene chloride (0.3 mL) was stirred at room temperature for 15 min., then the solution of 7 (6 mg, 27 μmol) in methylene chloride (0.15 mL) was added followed by TPAP (0.8 mg). The resulted dark mixture was stirred for 30 min., diluted with methylene chloride and applied on a silica Sep-Pak (2 g). Elution with hexane/ethyl acetate (96:4) gave a pure ketone 8 (3.5 mg, 59%). 8: [α]24D−43° (c 0.18 CHCl3); 1H NMR (500 MHz, CDCl3) δ 0.721 (3H, s, 18-H3), 0.825 (3H, t, J=7.3 Hz, 23-H3), 0.872 and 0.945 (3H and 3H, each s, 20-CH3 and 21-H3), 2.41 (1H, dd, J=11.0, 7.5 Hz, 14α-H).

Workup

  1. washElution with hexane/ethyl acetate (96:4)

Sources & evidence

ORD record
ord-76b0adc1964e440ea0e036d994994305
Source dataset
uspto-grants-2010_07
Patent number
US07763598B2

Reaction notes

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