Triethylamine → HCID 86591141, compound

HRID 1391507Notes

Reaction equation

HRID 1391507 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C@H:16]2[OH:28])[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N([CH2:34][CH3:35])CC)C.CN([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41]N=1)C.[OH-].[NH4+].C([O:50][CH2:51][CH3:52])(=O)C>C(#N)C>[C:43]1([C:35]2[CH:34]=[CH:13][CH:14]=[CH:9][CH:10]=2)[CH:44]=[CH:39][C:52]([C:51]([O:28][C@@H:16]2[C@@H:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=3)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]2)=[O:50])=[CH:41][CH:42]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 218852-DimethylaminopyridineHCID 11223524HCID 11223524, compound

Product 1

HCID 86591141HCID 86591141, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The (+/−)-tert-butyl (3S,4S)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-hydroxypiperidine-1-carboxylate (206 mg, 0.51 mmol), 1′-biphenyl-4-carbonyl chloride (540 mg, 2.50 mmol), triethylamine (400 mg, 4.00 mmol), and a catalytic amount of dimethylaminopyridine (10.0 mg, 0.08 mmol) was mixed together in acetonitrile (10.0 mL) at room temperature for 16 H. Ammonium hydroxide solution (5 mL) was added to the solution and it was stirred for 1 H. The heterogeneous solution was poured into ethyl acetate (50 mL) and hexanes (5 mL). The solution was extracted with 1N aqueous hydrochloric acid (2×10 mL), extracted with saturated aqueous sodium bicarbonate (2×10 mL), and extracted with saturated with saturated aqueous ammonium chloride (2×10 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The (+/−)-tert-butyl (3R,4R)-3-[(1,1′-biphenyl-4-ylcarbonyl)oxy]-4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)piperidine-1-carboxylate (164 mg, 0.28 mmol) was isolated as a semisolid by radial silica gel chromatography (25% ethyl acetate/hexanes). HRMS m/z 588.3150 (calcd for M+H 588.3140.)

Workup

  1. extractionThe solution was extracted with 1N aqueous hydrochloric acid (2×10 mL)
  2. extractionextracted with saturated aqueous sodium bicarbonate (2×10 mL)
  3. extractionextracted with saturated with saturated aqueous ammonium chloride (2×10 mL)
  4. dry with materialThe solution was dried over sodium sulfate and solvent
  5. customremoved at reduced pressure

Sources & evidence

ORD record
ord-9d6c5138de224fdfbbbc25b7e099319f
Source dataset
uspto-grants-2008_03
Patent number
US07338965B2

Reaction notes

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