Triphenylphosphine → 1,1-Dimethylethyl 4-[({4-[6-(methylsulfonyl)-3-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate	HCID 2764081	—
Reactant	4-(6-(Methylsulfonyl)pyridin-3-yl)phenol	HCID 57457980	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	1,1-Dimethylethyl 4-[({4-[6-(methylsulfonyl)-3-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate	HCID 24994335	76.1%

Reaction Steps

The title compound (0.34 g, 75%) was prepared as a white solid from 4-[6-(methylsulfonyl)-3-pyridinyl]phenol (0.25 g, 1.00 mmol), N-Boc-4-piperidinemethanol (0.23 g, 1.00 mmol) and Ph3P (0.27 g, 1.00 mmol) in THF (6 mL) followed by diisopropyl azodicarboxylate (0.22 g, 94%, 1.0 mmol) in THF (2 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CD3OD): δ 8.96 (d, 1H, J=2.2 Hz), 8.28 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.70 (d, 2H, 8.8 Hz), 7.08 (d, 2H, J=8.8 Hz), 4.20-4.10 (m, 2H), 3.92 (d, 2H, J=6.1 Hz), 3.24 (s, 3H), 2.90-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (2H); LRMS (APCI), m/z 469 (M+Na).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08101634B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-6bcc72322b2a428884c7f398463d9874
Source note	uspto-grants-2012_01