Methyl morpholine oxide → HCID 86762182, compound

HRID 1912741Notes

Reaction equation

HRID 1912741 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][S:9][C@@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[CH:12]([C:13](=[CH2:30])[CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:29])[CH2:11]1)=[O:4].C[N+]1([O-])CC[O:37]CC1>CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[F:32][C:2]([F:1])([F:31])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][S@@:9]([C@@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[CH:12]([C:13](=[CH2:30])[CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:29])[CH2:11]1)=[O:37])=[O:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86762183HCID 86762183, compound

Product 1

HCID 86762182HCID 86762182, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3α-(3-trifluoroacetamidopropylthio)-6-methyleneandrostane-17-one (Prepn. 82, 286 mg) in dry CH3CN (14 mL), NMO (213 mg) and molecular sieves (4 Å, 280 mg) were added followed by the addition of TPAP (10.6 mg). After 1 h at room temperature the mixture was evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 65/35) to give 3α-[(S)-3-trifluoroacetamidopropylsulfinyl]-6-methyleneandrostane-17-one (100 mg, 34% yield). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 9.43 (1H, bb), 4.72 (1H, m), 4.41 (1H, m), 3.24 (3H, m), 2.50-0.86 (24H, m), 0.75 (3H, s), 0.65 (3H, s).

Workup

  1. customAfter 1 h at room temperature the mixture was evaporated to dryness
  2. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 65/35)

Sources & evidence

ORD record
ord-0631bbd5c3ef4545b90b0fdd4abb4bd1
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

Loading…