Hydrogen Peroxide → HCID 54521082, compound

HRID 2072459Notes

Reaction equation

HRID 2072459 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][CH:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19]4=[O:28])[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][C@H:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C@H:19]4[OH:28])[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 214082211-Phenyl-8-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 54521082HCID 54521082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1-Phenyl-8-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one (5.0 g) is dissolved in 60 ml of dry tetrahydrofuran and added, dropwise, to a flask charged with 2.1 equivalents of a 1 molar tetrahydrofuran solution of lithium tri-sec-butylborohydride, previously cooled to -78° C, all under an argon atmosphere. The resulting solution is stirred for 16 hours at room temperature. The reaction mixture is treated at 0° C with 15 ml of 3 molar sodium hydroxide followed by the addition of 15 ml of 30% hydrogen peroxide. The aqueous phase is saturated with potassium carbonate and the organic layer is separated and concentrated. The residue is dissolved in methylene chloride, washed with water, dried and concentrated producing the crude product. Recrystallization of this material from methylene chloride/hexane yields 4.2 g of isomerically pure title compound, melting point 204°-205° C.

Workup

  1. additionadded
  2. customthe organic layer is separated
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customproducing the crude product
  9. customRecrystallization of this material from methylene chloride/hexane

Sources & evidence

ORD record
ord-8fdc1bfa7b794789be38be12786ac19a
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

Loading…