Aluminium lithium hydride → HCID 66757690, compound

HRID 1983692Notes

Reaction equation

HRID 1983692 reaction equation
C[O:2][C:3]([C:5]1([CH3:41])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)([OH:11])[CH2:9][CH2:8][N:7]([CH2:19][CH2:20][CH:21]=[C:22]2[C:28]3[CH:29]=[CH:30][CH:31]=[N:32][C:27]=3[CH2:26][O:25][C:24]3[CH:33]=[CH:34][C:35]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:36][C:23]2=3)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2([OH:11])[CH2:9][CH2:8][N:7]([CH2:19][CH2:20][CH:21]=[C:22]3[C:28]4[CH:29]=[CH:30][CH:31]=[N:32][C:27]=4[CH2:26][O:25][C:24]4[CH:33]=[CH:34][C:35]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:36][C:23]3=4)[CH2:6][C:5]2([CH2:3][OH:2])[CH3:41])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66758232HCID 66758232, compound

Product 1

HCID 66757690HCID 66757690, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Chloro-phenyl)-4-hydroxy-1-{3-[7-(hydroxyl-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-3-methyl-piperidine-3-carboxylic acid methyl ester (0.250 g, 0.43 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added LiAlH4 (1.3 mL, 1.3 mmol) dropwise and the reaction was allowed to stir at 0° C. for 3 h. The reaction was quenched with ice water slowly and diluted with ethyl acetate. The reaction mixture was allowed to stir at room temperature for 45 min. to break up any aluminum complexes. The organics were separated and the aqueous layer was extracted (2×) more. All of the organics were collected, dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (50% ethyl acetate/50% hexane to 75% ethyl acetate/25% hexane) to yield the title compound (0.103 g, 43%). 1H-NMR (CDCl3): δ 0.53 (s, 3H), 1.55 (d, 6H), 1.62 (m, 1H), 2.40 (q, 2H), 2.55 (q, 3H), 2.72-2.86 (m, 4H), 3.19 (dd, 1H), 3.24 (d, 1H), 3.41 (d, 1H), 5.33 (bs, 2H), 6.17 (t, 1H), 6.44 (bs, 1H), 6.79 (d, 1H), 7.17 (d, 1H), 7.26-7.59 (m, 7H), 8.50 (d, 1H). ESI-MS m/z: 549 (M+1), retention time 1.39.

Workup

  1. customThe reaction was quenched with ice water slowly
  2. additiondiluted with ethyl acetate
  3. stirringto stir at room temperature for 45 min.
  4. customThe organics were separated
  5. extractionthe aqueous layer was extracted (2×) more
  6. customAll of the organics were collected
  7. dry with materialdried over Mg2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. custompurified by Biotage flash chromatography (50% ethyl acetate/50% hexane to 75% ethyl acetate/25% hexane)

Sources & evidence

ORD record
ord-68a772b365e44274b2c0c37878c3055d
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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