Aluminium lithium hydride → HCID 178520973, compound

HRID 2279334Notes

Reaction equation

HRID 2279334 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][CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)[CH2:13][CH2:12]1)=O>O1CCCC1>[O:23]1[C:22]2[CH:27]=[CH:28][C:19]([CH2:18][NH:17][C@H:14]3[CH2:15][CH2:16][C@H:11]([CH2:9][OH:8])[CH2:12][CH2:13]3)=[CH:20][C:21]=2[O:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178501211HCID 178501211, compound

Product 1

HCID 178520973HCID 178520973, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (1.0 M solution in tetrahydrofuran, 2.20 mL, 2.20 mmol, 2.0 eq) is added at 0° C. to a stirred solution of trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexanecarboxylic acid methyl ester (355 mg, 1.10 mmol, 1.0 eq) in tetrahydrofuran (30 mL). After 2 hours stirring at 0° C., the reaction mixture is cautiously quenched with ice-water (6 mL). Tetrahydrofuran is evaporated and the crude is extracted with ethyl acetate (3×50 mL) and water (50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford {trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexyl}-methanol as an orange oil (322 mg, 99% yield).

Workup

  1. customthe reaction mixture is cautiously quenched with ice-water (6 mL)
  2. customTetrahydrofuran is evaporated
  3. extractionthe crude is extracted with ethyl acetate (3×50 mL) and water (50 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a313c98a11ed419db217bded4bb01688
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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