Diisopropylethylamine → HCID 89852507, compound

HRID 627288Notes

Reaction equation

HRID 627288 reaction equation
[CH2:1]([O:4][NH:5][C@@H:6]1[CH:11]=[C:10]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:9]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[NH:8][CH2:7]1)[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.Cl[C:41](Cl)([O:43]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:41](=[O:43])[N:8]2[CH2:7][C@H:6]1[CH:11]=[C:10]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:16])[CH3:17])[C@H:9]2[CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429Triphosgene2×HCID 131735305HCID 131735305, compound2×

Product 1

HCID 89852507HCID 89852507, compoundYield 260%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of O-allyl-N-((3R)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine (Intermediate 284, 3.95 g, 8.65 mmol) and diisopropylethyl amine (6.02 mL, 34.58 mmol) in acetonitrile (600 mL) at 0° C. was added triphosgene (0.871 g, 2.94 mmol) as a solution in acetonitrile (26 mL). The triphosgene solution was added at a rate of 4 mL/hour. Once addition was complete the reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and 1:1 brine:water. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-30% ethyl acetate/hexanes) afforded the title compound as a yellow oil (3.69 g, 88%). This reaction was run in two separate 1 L flasks due to the large volume and combined for work up and purification.

Workup

  1. additionOnce addition
  2. washwashed with saturated sodium bicarbonate and 1:1 brine
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0357302a61364e7ab602114fefa43634
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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