HCID 14302855, compound → HCID 57311524, compound

HRID 380640Notes

Reaction equation

[O:1]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C@:23]([OH:31])([CH2:29][OH:30])[CH2:24]2)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[C:40](Cl)=[O:41])=[CH:35][CH:34]=1>N1C=CC=CC=1>[O:1]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C@@:23]([CH2:29][O:30][C:40](=[O:41])[N:39]([C:36]1[CH:37]=[CH:38][C:33]([F:32])=[CH:34][CH:35]=1)[C:43]1[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=1)([OH:31])[CH2:24]2)[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2R)-5-t-butyldiphenylsiloxy-2-hydroxy-2-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalene (0.49 g) and N,N-di(4-fluorophenyl)carbamoyl chloride (1.08 g) in pyridine (2.3 ml) was stirred at 100° C. for 1.5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, 1N-HCl, and evaporated in vacuo. The residue was purified by chromatography on silica gel (50 ml) using a mixture of AcOEt and n-hexane to give (2R)-5-t-butyldiphenylsiloxy-2-{[N,N-di(4-fluorophenyl)-carbamoyloxy]methyl}-2-hydroxy-1,2,3,4-tetrahydronaphthalene (0.356 g) as an oil.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with water, 1N-HCl
customevaporated in vacuo
customThe residue was purified by chromatography on silica gel (50 ml)
additiona mixture of AcOEt and n-hexane

Sources & evidence

ORD record: ord-f638709005ae4901ab614fb031866db8
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303649B1

Reaction notes

Loading…