Phenol → HCID 131733439, compound

HRID 2277053Notes

Reaction equation

C1(O)C=CC=CC=1.[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=1)[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].CS(O[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[N:40]=1)(=O)=O>CN(C=O)C.CCOC(C)=O>[OH:8][C@@H:9]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[N:40]=2)[CH:21]=1)[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 90 °C

Procedure

Phenol (7, Intermediate I) (0.50 g, 1.87 mmol) and K2CO3 (1.29 g, 9.35 mmol) were added to a solution of (6-methylpyridin-2-yl)methyl methanesulfonate (412 mg, 2.05 mmol) in DMF (20 mL) and the reaction mixture was heated under reflux at 90° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with water and brine. Drying over anhydrous Na2SO4 and concentration under reduced pressure gave (R)-tert-butyl (3-hydroxy-3-(3-((6-methylpyridin-2-yl)methoxy)phenyl)propyl)carbamate as pale yellow liquid. Yield (200 mg, 72%); 1H NMR (400 MHz, CDCl3); δ 7.59 (t, J=8.0 Hz, 1H), 7.32 (d, J=7.2 Hz, 1H), 7.23 (s, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.03 (s, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.87 (dd, J=8.0, 2.4 Hz, 1H), 5.17 (s, 2H), 4.86 (bs, 1H), 4.71 (bs, 1H), 3.49-3.48 (m, 1H), 3.19-3.11 (m, 2H), 2.57 (s, 3H), 1.88-1.82 (m, 2H), 1.45 (s, 9H); MS: m/z 373.20 [M+H]+.

Workup

temperaturethe reaction mixture was heated
washwashed with water and brine
dry with materialDrying over anhydrous Na2SO4 and concentration under reduced pressure

Sources & evidence

ORD record: ord-2908a832ad1b4248a75f860e843fd9aa
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133154B2

Reaction notes

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