Aluminium lithium hydride → HCID 42600288, compound

HRID 875270Notes

Reaction equation

HRID 875270 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[C:19](=O)[O:18][C@H:17]3[C:21]4[C@@:26]([CH3:29])([CH2:27][CH2:28][C:16]23[OH:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH3:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH2:19][O:18][C@H:17]3[C:21]4[C@@:26]([CH3:29])([CH2:27][CH2:28][C:16]23[OH:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH3:30])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 42599313HCID 42599313, compound

Product 1

HCID 42600288HCID 42600288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of compound of example 27 (424 mg, 1 mmol) in THF (20 mL) under stirring to 0° C., under nitrogen, was added LAH (132.8 mg, 3.5 mmol) and stirred at room temperature (25° C.) for 15 hours. The reaction mixture was quenched with water (3×50 mL), stirred for 10-15 minutes and added ethyl acetate (3×100 mL). The separated ethyl acetate layer was dried over sodium sulphate. The product was obtained by concentrating the ethyl acetate portion. It was dried under vacuum. Crude product was washed with petroleum ether which was crystallized using ethyl acetate (2 mL) and petroleum ether (5-6 drops) to obtain the title compound.

Workup

  1. customThe reaction mixture was quenched with water (3×50 mL)
  2. stirringstirred for 10-15 minutes
  3. additionadded ethyl acetate (3×100 mL)
  4. dry with materialThe separated ethyl acetate layer was dried over sodium sulphate
  5. customThe product was obtained
  6. concentrationby concentrating the ethyl acetate portion
  7. customIt was dried under vacuum
  8. washCrude product was washed with petroleum ether which
  9. customwas crystallized

Sources & evidence

ORD record
ord-080c3c5cb39f453887d68578a6a66fa6
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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