HCID 13720638, compound → HCID 89485839, compound

HRID 1469400Notes

Reaction equation

HRID 1469400 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C([Li])CCC.[CH:18]([CH:20]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:22][CH2:21]1)=[O:19]>C1COCC1>[OH:19][CH:18]([C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[S:3][CH2:4][CH2:5][CH2:6][S:1]1)[CH:20]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH:23]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 13720638HCID 13720638, compoundHCID 77230831HCID 77230831, compoundHCID 178418339Butyllithium

Product 1

HCID 89485839HCID 89485839, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(1,3-dithian-2-yl)pyridine (2.86 g, 14.51 mmol) in THF (80 ml) was added n-butyllithium (6.77 ml, 2.5 M, 16.93 mmol) by syringe at −78° C. The mixture was stirred at −78° C. for 0.5 h, then tert-Butyl 5-formyl-2-phenylpiperidine-1-carboxylate (3.5 g, 12.10 mmol) in THF (15 ml) was added via syringe. The mixture was stirred at −78° C. for 1 h, then quenched with aqueous NH4Cl, and diluted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. LC-MS m/e 487.03 [M+1]+.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 h
  2. customquenched with aqueous NH4Cl
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6715e882aa654bf684409b247de3942c
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

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