Sodium hydride → HCID 67061784, compound

HRID 910801Notes

Reaction equation

HRID 910801 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1.[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][OH:59].[H-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][O:59][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 56924404(2R)-3-Methoxy-2-methylpropan-1-olHCID 67061878HCID 67061878, compound

Product 1

HCID 67061784HCID 67061784, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 mmol of 6-[(3R,4R,6S)-4-(4-chloromethyl-phenyl)-1-(toluene-4-sulfonyl)-6-triisopropylsilanyloxymethyl-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine, 1.5 mmol of (R)-3-methoxy-2-methyl-propan-1-ol [911855-78-2] and 0.1 mmol of TBAI in 5 ml of DMF are added 1.65 mmol of NaH (55% in dispersion oil) at 0° C. The reaction mixture is allowed to warm to RT and stirred overnight, diluted with water, extracted with TBME and the organic phase is dried over Na2SO4. The organic phase is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a pale yellow oil. Rf=0.20 (EtOAc/heptane 1:2).

Workup

  1. extractionextracted with TBME
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationThe organic phase is concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-148c59c4412a476eae5d580d264cff43
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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