Triphenylphosphine → HCID 86610263, compound

HRID 1787933Notes

Reaction equation

HRID 1787933 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O-:11])=[O:10])=[C:7]([OH:14])[CH:6]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28]O)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28][O:14][C:7]2[CH:6]=[C:5]([O:4][CH2:3][CH2:2][F:1])[CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH3:30])=[O:10])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 178524495HCID 178524495, compound

Product 1

HCID 86610263HCID 86610263, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that of Example 26-B, 4-(2-fluoroethoxy)-2-hydroxybenzoate (2.6 g, 12.8 mmol), 1-tert-butoxycarbonylpiperidin-3-ylmethanol (2.76 g, 12.8 mmol), and triphenylphosphine (4.02 g, 15.4 mmol) in THF (50 mL) is treated with diethyl azodicarboxylate (2.59 g, 12.8 mmol) in THF to afford methyl 2-(1-tert-butoxycarbonyl-piperidin-3-ylmethoxy)-4-(2-fluoroethoxy)benzoate (6.35 g) which is used without further purification.

Sources & evidence

ORD record
ord-445ff504caa7472293b9a6f54b4d2ea7
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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