Water → HCID 59900574, compound

HRID 2228798Notes

Reaction equation

HRID 2228798 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]([NH2:19])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.O>O1CCCC1.C(OCC)(=O)C>[NH3:12].[CH:7]1([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:17][NH2:19])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 45116162HCID 45116162, compound

Product 2

HCID 222AmmoniaHCID 59900574HCID 59900574, compoundYield 140.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminium hydride (2.63 ml, 1M in tetrahydrofuran, 2.63 mmol) was added dropwise to a solution of (2R)-1-cyclopentyl-2-pyrrolidinecarboxamide (preparation 142) (320 mg, 1.76 mmol) in tetrahydrofuran (5 ml), and once addition was complete, the reaction was stirred at room temperature for 4 hrs. Water was added to quench the reaction, the mixture diluted with ethyl acetate and dried over MgSO4 This mixture was filtered through Whatman® fibre, and the filtrate evaporated under reduced pressure. The residue was purified by chromatography using a Biotage™ (KP-Sil™ 60 Å silica gel) cartridge and an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5 to 90:10:1) to give the desired product as a clear oil, (208 mg, 71%).

Workup

  1. customto quench
  2. customthe reaction
  3. dry with materialdried over MgSO4 This mixture
  4. filtrationwas filtered through Whatman® fibre
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-68a3ca7c8acb424184cfb76f8d1aaac8
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

Loading…