Pyridine → (R)-2-Bromo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol

HRID 907076Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:16]([OH:19])[CH2:17][Br:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C@@H:16]([OH:19])[CH2:17][Br:18])=[CH:3][C:2]=1[NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of (1R)-1-[3-amino-4-(benzyloxy)phenyl]-2-bromoethanol (Org. Process Research and Development, 1998, 2, 96)_(30.8 g, 95.6 mmol) in dichloromethane (300 ml) was treated with pyridine (9.3 ml, 115 mmol). The resulting solution was cooled to 5° C. and a solution of methanesulfonyl chloride (7.8 ml, 100.7 mmol) in dichloromethane (10 ml) added dropwise. The mixture was stirred at 5° C. for a further 30 minutes and then allowed to warm gradually to room temperature over a period of 16 hours. The reaction mixture was washed with 2N hydrochloric acid (110 ml) and the organic phase separated, dried (magnesium sulfate) and the solvent removed in vacuo to give an orange oil. The residue was crystallized from hot toluene (100 ml) to give the title compound as a pale pink solid (33.7 g).

Workup

temperatureto warm gradually to room temperature over a period of 16 hours
washThe reaction mixture was washed with 2N hydrochloric acid (110 ml)
customthe organic phase separated
dry with materialdried (magnesium sulfate)
customthe solvent removed in vacuo
customto give an orange oil
customThe residue was crystallized from hot toluene (100 ml)

Sources & evidence

ORD record: ord-5bf8180cdced4bc9964b692b646b4017
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013019B2

Reaction notes

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