Hydrogen Peroxide → HCID 20701211, compound

HRID 428319Notes

Reaction equation

HRID 428319 reaction equation
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[CH2:5][CH2:6][C@H:7]([C:14]1[CH:19]=[C:18]([CH:20]=[CH2:21])[CH:17]=[CH:16][C:15]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].B1C2CCCC1CCC2.[OH-:42].[Na+].OO>C1COCC1.O>[CH:30]([N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6][C@H:7]([C:14]1[CH:19]=[C:18]([CH2:20][CH2:21][OH:42])[CH:17]=[CH:16][C:15]=1[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 53709387HCID 53709387, compound

Product 1

HCID 20701211HCID 20701211, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-N,N-Diisopropyl-3-(2-benzyloxy-5-ethenylphenyl)-3-phenylpropanamine (1 g, 2.34 mmol) in THF (25 mL) was added to 9-BBN (0.5 M in THF, 11.7 mL, 5.85 mmol) under nitrogen atmosphere at 0° C. Additional 9-BBN (2.3 mL, 1.2 mmol) was added after 3 hours of stirring, the temperature was raised to room temperature and the mixture was stirred for 0.5 hour. It was then cooled to 0° C. and 1 M sodium hydroxide (10 mL) was added followed by H2O2 (30% in H2O, 10 mL). After 1 hours stirring, water was added and the mixture was extracted with diethyl ether. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica (gradient of diethyl ether to 1% NH3 in diethyl ether). Yield 0.67 g (64%). 1H NMR (CDCl3) δ0.90 (d, 12H), 2.10-2.18 (m, 2H), 2.30-2.37 (m, 2H), 2.80 (t, 2H), 2.90-3.0 (m, 2H), 3.80 (br, 2H), 4.40 (t, 1H), 5.0 (s, 2H), 6.80 (d, 1H), 7.0 (m, 1H), 7.10-7.38 (m, 11H).

Workup

  1. stirringthe mixture was stirred for 0.5 hour
  2. temperatureIt was then cooled to 0° C.
  3. stirringAfter 1 hours stirring
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica (gradient of diethyl ether to 1% NH3 in diethyl ether)

Sources & evidence

ORD record
ord-e15e10862415498b865243ba2f93e52d
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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