Water → HCID 86694782, compound

HRID 2404600Notes

Reaction equation

HRID 2404600 reaction equation
O.C[Si]([Cl:6])(C)C.[OH:7][C:8]1[CH:9]=[C:10]([C@@:14]2([OH:35])[C@H:19]([CH2:20][N:21]([CH3:30])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:18]3[CH2:31][C@@H:16]([C:17]3([CH3:33])[CH3:32])[C@H:15]2[CH3:34])[CH:11]=[CH:12][CH:13]=1>CC(=O)CC>[ClH:6].[OH:7][C:8]1[CH:9]=[C:10]([C@@:14]2([OH:35])[C@H:19]([CH2:20][N:21]([CH3:30])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:18]3[CH2:31][C@@H:16]([C:17]3([CH3:32])[CH3:33])[C@H:15]2[CH3:34])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60142342HCID 60142342, compound

Product 1

HCID 86694782HCID 86694782, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (4 mg, 0.25 mmol) and TMSCl (27 mg, 0.25 mmol) to a solution of (1R,2R,3S,4S,5S)-3-(3-hydroxyphenyl)-2,6,6-trimethyl-4-((methyl(phenethyl)amino)methyl)bicyclo[3.1.1]heptan-3-ol (100 mg, 0.25 mmol) in 2-butanone (5 mL). Stir the reaction mixture at room temperature for 3 hours. After removal solvent by evaporation, wash the residue with EtOAc (1 mL×2) and dry under vacuum to give (1R,2R,3S,4S,5S)-3-(3-hydroxyphenyl)-2,6,6-trimethyl-4-((methyl(phenethyl)amino)methyl)bicyclo[3.1.1]heptan-3-ol hydrochloride (93 mg, Yield: 85.3%) as white solid. 1H NMR (400 MHz, D2O) δ 7.21-7.32 (m, 7H), 7.97-7.99 (d, J=7.2, 1H), 6.71-6.78 (dd, J1=8.0, J2=22.0, 1H), 2.86-3.33 (m, 5H), 2.43-2.68 (m, 7H), 2.11-2.20 (m, 2H), 1.73-1.75 (m, 1H), 1.23-1.25 (d, J=5.6, 3H), 1.04-1.05 (d, J=4.4, 3H), 0.69-0.71 (d, J=5.6, 3H). [α]D20=−8.6 (c=1.4 mg/mL, MeOH).

Workup

  1. customAfter removal solvent
  2. customby evaporation
  3. washwash the residue with EtOAc (1 mL×2)
  4. customdry under vacuum

Sources & evidence

ORD record
ord-376bc7064d9542f98396b05cfd12a682
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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