Aluminium lithium hydride → HCID 66941293, compound

HRID 1363864Notes

Reaction equation

HRID 1363864 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=O)[NH:11][C@H:10]([CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:9]1=O)[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][NH:11][C@H:10]([CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[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 66941658HCID 66941658, compound

Product 1

HCID 66941293HCID 66941293, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of compound 32 (1.153 g, 3.62 mmol) in dry THF (60 mL) on ice was added LiAlH4 (0.566 g, 14.89 mmol). The mixture was then heated at reflux for 2 h. The solution was cooled, stirred 1 h then the excess LiAlH4 was quenched by the sequential addition of 0.6 mL water, 1.2 mL 4 M NaOH solution and 0.6 mL water. The solids that formed will filtered (Celite) and the filtrate concentrated to give 33 as a pale colored oil (1.076 g, 99% yield). 1H NMR (400 MHz, CDCl3): δ 1.44-1.62 (m, 4H), 1.64-1.74 (m, 1H), 1.74-1.94 (m, 2H), 2.08-2.17 (m, 1H), 2.35 (bs, 1H, NH), 2.71-2.79 (m, 2H), 2.87-2.95 (m, 1H), 2.95-3.08 (m, 2H), 3.26 (m, 0.5H), 3.36 (dd, J=4.0, 9.9 Hz, 0.5H), 3.45-3.52 (m, 3H), 3.61-3.73 (m, 1H), 3.78-3.86 (m, 1H), 4.56 (m, 1H); 3C NMR (100 MHz, CDCl3): δ 19.4, 19.5, 25.3, 30.5, 45.1, 53.4, 53.5, 54.5, 54.7, 55.7, 62.2, 62.4, 63.3, 69.5, 69.9, 98.8, 99.5, 127.0, 128.2, 129.1, 137.9.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 h
  3. temperatureThe solution was cooled
  4. customthe excess LiAlH4 was quenched by the sequential addition of 0.6 mL water, 1.2 mL 4 M NaOH solution and 0.6 mL water
  5. customThe solids that formed will
  6. filtrationfiltered (Celite)
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-650369bd1124453889e6cf3535cf79fe
Source dataset
uspto-grants-2011_02
Patent number
US07887784B2

Reaction notes

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