tert-Butanol → 2-Chloro-5-(2,3-dihydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1765539Notes

Reaction equation

HRID 1765539 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19](CC=C)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[C:25]([OH:29])(C)([CH3:27])[CH3:26].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:51]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:26][CH:25]([OH:29])[CH2:27][OH:51])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 211074042-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 211074032-Chloro-5-(2,3-dihydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (prepared as described in Example 5a) (1.99 g), tert-butanol (40 mL) and water (40 mL) were stirred together under nitrogen and AD-mix-α was added. The mixture was then stirred at room temperature for 20 hours. Sodium sulfite (2 g) was added and the mixture was stirred for 10 minutes. Water (100 mL) and ethyl acetate (100 mL) were then added. The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×100 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. Purification was performed by column chromatography eluting with 5:95 methanol/ethyl acetate to give the sub-titled compound as a solid (1.77 g).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification
  9. washeluting with 5:95 methanol/ethyl acetate

Sources & evidence

ORD record
ord-61eaf422c0c44f159702fbf59b06ac97
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

Loading…