Methanol → HCID 12709721, compound

HRID 1018627Notes

Reaction equation

HRID 1018627 reaction equation
FC(F)(F)[C:3]1[CH:4]=[C:5]([CH:26]=[C:27](C(F)(F)F)[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1(C)C=CC=CC=1>[CH2:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:15](=[O:16])[NH:14][CH:13]([OH:17])[CH:12]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:24][CH2:25]1)[C:5]1[CH:4]=[CH:3][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 59872176HCID 59872176, compound

Product 1

HCID 12709721HCID 12709721, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(rac)-8-Benzyl-4-phenyl-2,8-diaza-spiro[4.5]decane-1,3-dion (10.0 g, 30 mmol synthesis described in example 156) was dissolved in toluene (200 mL). Diisobutyl aluminium hydride (220 mL, 1M in THF, 220 mmol) was slowly added while cooling with an ice bath so that the reaction temperature did not exceed 10° C. The reaction mixture was stirred at room temperature for 2 days. A mixture of methanol (6 mL) and water (6 mL) was added at room temperature. The resulting gel was filtered through dicalit and washed with methylene chloride. The filtrate was evaporated to give 8-benzyl-3-hydroxy-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one as a mixture of diastereomers (8.0 g, 80%).

Workup

  1. temperaturewhile cooling with an ice bath so that the reaction temperature
  2. customdid not exceed 10° C
  3. additionwas added at room temperature
  4. filtrationThe resulting gel was filtered through dicalit
  5. washwashed with methylene chloride
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-cab9f922763142e886fb90fb66221b76
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

Loading…