Sodium hydride → HCID 86619737, compound

HRID 1921207Notes

Reaction equation

HRID 1921207 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[CH2:5][CH2:4]1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C>[O:17]=[C:9]1[C:6]2([CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]1[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 39240582Spiro[indole-3,4'-oxan]-2(1H)-one

Product 1

HCID 86619737HCID 86619737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (8.00 mg of a 60% dispersion in mineral oil, 0.207 mmol) was added to a solution of 2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-pyran]-2(1H)-one from Step A (35.0 mg, 0.172 mmol) in DMF (1 mL) at 0° C. After 1 hr, tert-butyl bromoacetate (0.280 mL, 0.189 mmol) was added and the reaction warmed to ambient temperature. After 18 h, the reaction was partitioned between CH2Cl2 (10 mL) and saturated NH4Cl (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=318 (M+1).

Workup

  1. waitAfter 18 h
  2. customthe reaction was partitioned between CH2Cl2 (10 mL) and saturated NH4Cl (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f016b5247c344017905fa0fd380c8a35
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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