HCID 21075363, compound → 2-Amino-4-[3-[(tetrahydro-2H-pyran-2-yl)oxy]propyl]phenol

HRID 1373755Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:11][C:10]=1[N+:25]([O-])=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[NH2:25][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of Example 68B (1.19 g, 3.25 mmol), 20% Pd(OH)2/C (100 mg), and ethanol (50 mL) were stirred, and heated at 50° C. for 2 hours under H2 atmosphere (60 psi). The solution was filtered, dried with silica gel powder (8 g), and purified by flash chromatography eluting with 30% ethyl acetate in hexanes (1 L) and then with 1% methanol in ethyl acetate (1 L) to give the title compound (0.37 g, 45%). MS (DCI) m/z 252.05 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.46–1.62 (m, 4 H) 1.70 (m, 1 H) 1.76–1.90 (m, 3 H) 2.45–2.58 (m, 2 H) 3.37 (m, 1 H) 3.49 (m, 1 H) 3.71 (m, 1 H) 3.86 (m, 1 H) 4.55 (t, J=3.73 Hz, 1 H) 6.41 (dd, J=7.97, 2.20 Hz, 1 H) 6.59 (m, 1 H) 6.61 (s, 1 H).

Workup

filtrationThe solution was filtered
customdried with silica gel powder (8 g)
custompurified by flash chromatography
washeluting with 30% ethyl acetate in hexanes (1 L)

Sources & evidence

ORD record: ord-829ea9262bcc46448b1fd22e1cb6944e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163939B2

Reaction notes

Loading…