Aluminium lithium hydride → HCID 178516919, compound

HRID 2279331Notes

Reaction equation

HRID 2279331 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]2[CH:21]=[CH:22][C:23]3[S:28][CH2:27][C:26](=[O:29])[NH:25][C:24]=3[CH:30]=2)=[O:19])[CH2:13][CH2:12]1)=O>O1CCCC1>[OH:8][CH2:9][C@H:11]1[CH2:12][CH2:13][C@H:14]([NH:17][C:18]([C:20]2[CH:21]=[CH:22][C:23]3[S:28][CH2:27][C:26](=[O:29])[NH:25][C:24]=3[CH:30]=2)=[O:19])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178501228HCID 178501228, compound

Product 1

HCID 178516919HCID 178516919, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (1.0 M solution in tetrahydrofuran, 0.66 mL, 0.66 mmol, 2.0 eq) is added at 0° C. to a stirred solution of trans-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester (127 mg, 0.33 mmol, 1.0 eq) in tetrahydrofuran (2 mL). After 1 hour stirring at 0° C., the reaction mixture is cautiously quenched with ice-water (3 mL). Tetrahydrofuran is evaporated and the crude is extracted with ethyl acetate (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid (trans-4-hydroxymethyl-cyclohexyl)-amide as a yellow solid (47 mg, 40% yield).

Workup

  1. customthe reaction mixture is cautiously quenched with ice-water (3 mL)
  2. customTetrahydrofuran is evaporated
  3. extractionthe crude is extracted with ethyl acetate (3×10 mL) and water (10 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e12956aa1a64e4284dcabe60b134f63
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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