Sodium hydride → HCID 59268898, compound

HRID 2061595Notes

Reaction equation

HRID 2061595 reaction equation
[H-].[Na+].[OH:3][NH:4][C:5](=[NH:7])[CH3:6].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH:27]3[CH2:28][CH:29]([C:31](OCC)=O)[CH2:30][CH:19]2[CH2:20][C:21]2([CH2:26]3)[O:25][CH2:24][CH2:23][O:22]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C1COCC1.CCOC(C)=O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH:27]3[CH2:28][CH:29]([C:31]4[O:3][N:4]=[C:5]([CH3:6])[N:7]=4)[CH2:30][CH:19]2[CH2:20][C:21]2([CH2:26]3)[O:25][CH2:24][CH2:23][O:22]2)(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 59268882HCID 59268882, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 59268898HCID 59268898, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60% dispersion, 43 mg, 1.09 mmol) was added to a solution of N-hydroxy acetamidine (81 mg, 1.09 mmol) in THF (2 mL) and the resulting mixture was stirred at 50° C. for 15 minutes. Ethyl 9-[(4-chlorophenyl)sulfonyl]spiro[9-azabicyclo[3.3.1]nonane-3,2′-[1,3]dioxolane]-7-carboxylate (50) (0.394 g, 0.916 mmol) in THF (2 mL) was added to the reaction mixture and the resulting solution was stirred at room temperature for 1 hour. The mixture was diluted with EtOAc and washed with H2O. The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to yield 0.40 g (quant.) of compound 51. MS (ESI) 440.1 (M+H).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 1 hour
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1bb45f89da90445ea52b9ae3b1ff28c7
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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