Aluminium lithium hydride → HCID 68027120, compound

HRID 527897Notes

Reaction equation

HRID 527897 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=O)OC(C)(C)C)[CH2:11]2)=[N:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:16][NH:15][C@@H:12]1[CH2:13][CH2:14][N:10]([C:4]2[C:5]3[CH:9]=[CH:8][NH:7][C:6]=3[N:1]=[CH:2][N:3]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68027129HCID 68027129, compound

Product 1

HCID 68027120HCID 68027120, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Under N2, to a solution of (R)-tert-butyl 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-ylcarbamate (380 mg, 1.34 mmol) in anhydrous THF (10 mL) was slowly added Lithium aluminium hydride (143 mg, 3.76 mmol) at 0° C. After the completion of the addition, the reaction mixture was stirred at 65° C. for 2 hours. The reaction mixture was then cooled to 0° C., quenched with aqueous NaOH (15%), and filtrated to remove the solid. The filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC to give the title compound (178 mg, 66% yield). MS (m/z): 218 (M+H)+.

Workup

  1. customat 0° C
  2. additionAfter the completion of the addition
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. customquenched with aqueous NaOH (15%)
  5. filtrationfiltrated
  6. customto remove the solid
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-3b31e276fd954aa1a56c930646848c16
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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