Benzene → HCID 86705566, compound

HRID 2279585Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](/[CH:12]=[CH:13]/[C:14]([N:16]2[C@H:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][O:18][C:17]2=[O:27])=[O:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CO[CH2:30][N:31]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][Si](C)(C)C.C(O)(C(F)(F)F)=O.C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:37]([N:31]1[CH2:32][C@@H:12]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[CH:3]=2)[C@H:13]([C:14]([N:16]2[C@H:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][O:18][C:17]2=[O:27])=[O:15])[CH2:30]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 338 (2.10 g, 5.54 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.98 mL, 7.75 mmol) dissolved in toluene (25 mL) and cooled to 0° C. A solution of TFA (0.0427 mL, 0.554 mmol) and benzene (1 mL) was added slowly over 15 min and the mixture was stirred for 4 h. The mixture was washed sequentially with satd. aq. NaHCO3, twice with water, dried, filtered and evaporated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (20-40% EtOAc) to afford 1.62 g (57.1%) of (R)-3-((3S,4R)-1-benzyl-4-(3-fluoro-4-(trifluoromethyl)phenyl)pyrrolidine-3-carbonyl)-4-phenyloxazolidin-2-one (340) as white foamy solid.

Workup

washThe mixture was washed sequentially with satd
dry with materialaq. NaHCO3, twice with water, dried
filtrationfiltered
customevaporated
customThe crude residue was purified by SiO2 chromatography
washeluting with an EtOAc/hexane gradient (20-40% EtOAc)

Sources & evidence

ORD record: ord-d68d6a5d46fc450098a05cfff3cf279c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133187B2

Reaction notes

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