Isopropanol → Methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-isopropoxybenzoate

HRID 644225Notes

Reaction equation

HRID 644225 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:31]=CC=C[CH:27]=1.C(O)(C)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([O:25][CH:26]([CH3:31])[CH3:27])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68532897Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-hydroxybenzoate

Product 1

HCID 68534342Methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-isopropoxybenzoateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-hydroxy-benzoate (0.735 g, 2.1 mmol), triphenylphosphine (0.551 g, 2.1 mmol), and isopropanol (0.158 mL, 2 mmol) in tetrahydrofuran was added diisopropyl azodicarboxylate (0.433 mL, 2.2 mmol) dropwise. The solution was sonicated for 30 minutes. The reaction mixture was purified without workup by RPLC (EtOAc/Hexane 3:7) to give 0.675 g (86%) of pure product.

Workup

  1. customThe solution was sonicated for 30 minutes
  2. customThe reaction mixture was purified without workup by RPLC (EtOAc/Hexane 3:7)

Sources & evidence

ORD record
ord-f439110719b44ed897e47425cc2004ae
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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