HCID 57918171, compound → HCID 59598487, compound

HRID 2266244Notes

Reaction equation

HRID 2266244 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:15]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[O:16])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=1.C[Si]1(C)CC[Si](C)(C)[N:32]1[CH2:38][CH2:39][CH2:40][Mg]Cl>C1COCC1>[NH2:32][CH2:38][CH2:39][CH2:40][C@:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1)([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=1)[OH:16]

Participants

4

Reactant 2

HCID 57918171HCID 57918171, compoundHCID 178504161HCID 178504161, compound

Product 1

HCID 59598487HCID 59598487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-tert-butyl 3-(6-chloro-3′-methylbiphenylcarbonyl)piperidine-1-carboxylate (800 mg, 1.94 mmol) in anhydrous THF (15 mL) cooled to −78° C. was added dropwise a solution of 2 M (3-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)propyl)magnesium chloride in THF (0.968 mL, 1.94 mmol). After addition, the reaction mixture was allowed to warm slowly to room temperature while stirring overnight. The mixture was quenched with satd aq NH4Cl (15 mL) and extracted with CH2Cl2 (3×). The combined organic layers were dried over Na2SO4 and concentrated to give crude (R)-tert-butyl 3-((S)-4-amino-1-(6-chloro-3′-methylbiphenyl-2-yl)-1-hydroxybutyl)piperidine-1-carboxylate (900 mg), which was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. customThe mixture was quenched with satd aq NH4Cl (15 mL)
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40320c8812d442af9003d03148ed87a3
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

Loading…