Water → HCID 64842474, compound

HRID 2360713Notes

Reaction equation

HRID 2360713 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14](=O)[C:9]21[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[Si](C)(C)C.O>C1COCC1>[CH2:1]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][CH2:14][C:9]21[CH2:10][CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 21226445Aluminium lithium hydrideHCID 866803356-Benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decan-10-one

Product 1

HCID 64842474HCID 64842474, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
55 °C

Procedure

Under Argon atmosphere to a solution of 10.78 g of 6-benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decan-10-one in 160 ml of THF 33 ml of a 2.4 M solution of lithium aluminium hydride in THF were slowly added. The reaction was heated to 55° C., and 5 ml of chlorotrimethylsilane were added dropwise. The reaction was kept at 55-60° C. for 2.5 h and then cooled to 0° C. 16 ml of water were added dropwise, and THF was added. The mixture was filtered by suction over celite and the filtrate was concentrated in vacuo. The product was precipitated by treatment with methyl tert-butyl ether. 9.47 g (93%) of the title compound were obtained.

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe mixture was filtered by suction over celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe product was precipitated by treatment with methyl tert-butyl ether

Sources & evidence

ORD record
ord-d656a166e42446d19edf28ab71225e61
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

Loading…