Acetone Cyanohydrin → HCID 59331350, compound

HRID 1882041Notes

Reaction equation

HRID 1882041 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32]O)=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CC(C)(O)[C:36]#[N:37].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][C:36]#[N:37])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59331365HCID 59331365, compound

Product 1

HCID 59331350HCID 59331350, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]methanol (0.500 g) in tetrahydrofuran (10 mL) were added acetone cyanohydrin (202 mg), tributylphosphine (466 mg) and 1,1′-(azodicarbonyl)dipiperidine (540 mg), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was suspended in ethyl acetate and filtered to remove the precipitate, and the filtrate, and the suspension was concentrated under reduced pressure. The residue was successively purified by silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio) and basic silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio), and recrystallized from hexane-ethyl acetate to give the title compound (0.116 g, yield 23%) as colorless crystals. MS: 476 (MH+). melting point 139-141° C.

Workup

  1. filtrationfiltered
  2. customto remove the precipitate
  3. concentrationthe filtrate, and the suspension was concentrated under reduced pressure
  4. customThe residue was successively purified by silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio) and basic silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio)
  5. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f926e838e96a45c980d8e281e4d2db48
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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