Methyl iodide → HCID 59268890, compound

HRID 2061600Notes

Reaction equation

HRID 2061600 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:22]3[CH2:23][CH:24]([C:26]4([OH:29])[CH2:28][CH2:27]4)[CH2:25][CH:14]2[CH2:15][C:16]2([CH2:21]3)[O:20][CH2:19][CH2:18][O:17]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.I[CH3:31]>C1COCC1.CCOC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH:14]3[CH2:25][CH:24]([C:26]4([O:29][CH3:31])[CH2:28][CH2:27]4)[CH2:23][CH:22]2[CH2:21][C:16]2([CH2:15]3)[O:20][CH2:19][CH2:18][O:17]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59268902HCID 59268902, compound

Product 1

HCID 59268890HCID 59268890, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 46 mg, 1.16 mol) was added to a solution of 1-{9-[(4-chlorophenyl)sulfonyl]spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolan]-7-yl}cyclopropanol (55) (321 mg, 0.775 mmol) in THF (2 mL). The resulting solution was stirred for 10 minutes, after which iodomethane (72 μL, 1.16 mmol) was added. The reaction mixture was stirred at room temperature for 18 h and was subsequently diluted with EtOAc and washed with brine. The organic phase was dried (Na2SO4), filtered, and concentrated to give 9-[(4-chlorophenyl)sulfonyl]-7-(1-methoxycyclopropyl)spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolane] (56). MS (ESI) 428.1 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. washwashed with brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d32d2f74352946559422a7772cc9887d
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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