tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamate → HCID 12988679, compound

HRID 1243282Notes

Reaction equation

HRID 1243282 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([C@@H:18]1[CH2:20][O:19]1)[CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1([CH3:40])[N:27]([C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[C@H:26]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[CH2:39][C@H:25]2[O:24]1.[Li]CCCC>C1COCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)[C@@H:18]([OH:19])[CH2:20][C@H:29]([C:28]([N:27]1[C@H:26]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[CH2:39][C@H:25]2[O:24][C:23]1([CH3:22])[CH3:40])=[O:32])[CH2:30][CH3:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11415322tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamateHCID 12988678HCID 12988678, compoundHCID 178418339Butyllithium

Product 1

HCID 12988679HCID 12988679, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(1S,2S)-[2-(3,5-Difluorophenyl)-1-oxiranylethyl]-carbamic acid tert-butyl ester (VI, 113 mg) and 1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-butan-1-one (VII, 94 mg) were combined in dry THF (3 mL), and cooled to −78° C. To this solution was added BuLi (2.5 M in hexanes, 0.32 mL) over 5 min., whereupon the solution was allowed to warm to 0° C. for 1.5 h. The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (20–30% EtOAc/hexanes) to give an oil: MH+559.1.

Workup

  1. temperatureto warm to 0° C. for 1.5 h
  2. customThe reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (20–30% EtOAc/hexanes)
  7. customto give an oil

Sources & evidence

ORD record
ord-4b0ced2d6a784e76a0c683e9eb357be8
Source dataset
uspto-grants-2006_10
Patent number
US07119085B2

Reaction notes

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