Sodium Hydroxide → HCID 11999035, compound

HRID 1364104Notes

Reaction equation

HRID 1364104 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:17])[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[S:9][C:5]=2[CH:4]([OH:17])[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6222625,5-DiMethyl-2-(Morpholin-4-yl)-5,6-dihydro-1,3-benzothiazol-7(4H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 11999035HCID 11999035, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 48 (0.13 g, 0.5 mmol) in THF (10 mL) at r.t. was added LiAlH4 (0.5 mL, 1M solution in THF, 0.5 mmol) dropwise. The reaction mixture was stirred at r.t. for 2 h and then poured into 10% NaOH solution (20 mL) and extracted with DCM (2×20 mL). The combined organic fractions were dried over MgSO4, filtered and the solvent removed by evaporation in vacuo. Purification by column chromatography gave the title compound (0.07 g, 52%) as a solid. δH (DMSO-d6) 5.23 (1H, d, J 6.5 Hz), 4.65 (1H, dt, J 8.1 and 6.7 Hz), 3.77-3.70 (4H, m), 3.39 (4H, m), 2.40-2.24 (2H, m), 1.84 (1H, dd, J 5.9 and 11.3 Hz), 1.48 (1H, dd, J 8.8 and 12.6 Hz), 1.09 (3H, s), 0.94 (3H, s). LCMS (ES+) 269.0 (M+H)+.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed by evaporation in vacuo
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-a37019d45bfd4022a4723d1c80da9d9c
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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