Lithium Hexamethyldisilazide → HCID 86682272, compound

HRID 540449Notes

Reaction equation

HRID 540449 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C@@H:12]([NH:29][C:30](=[O:39])[O:31]CC1C=CC=CC=1)[CH2:13][CH2:14][C@@H:15]1[C@@H:17]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([CH3:28])[CH:19]=2)O1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[C@H:12]1[N:29]2[C:30](=[O:31])[O:39][C@H:17]([C:18]3[CH:23]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:21]=[C:20]([CH3:28])[CH:19]=3)[C@@H:15]2[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 86682271HCID 86682271, compound

Product 1

HCID 86682272HCID 86682272, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To benzyl [(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]-3-{(2R,3R)-3-[3-methyl-5-(trifluoromethyl)phenyl]oxiran-2-yl}propyl]carbamate (100 mg, 0.162 mmol) in DMF (2 mL) was added LiHMDS (1.0 M, 0.324 mL, 0.324 mmol) at 0° C. The mixture was stirred at room temperature overnight and the solvent was removed under reduced pressure. The resultant residue was purified by preparative TLC to yield (1R,5S,7aS)-5-[2-bromo-5-(trifluoromethyl)phenyl]-1-[3-methyl-5-(trifluoromethyl)phenyl]tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one (75 mg, 0.148 mmol). 1H NMR (500 MHz, CDCl3) δ7.72 (m, 2H), 7.46 (s, 1H), 7.44 (d, J=8.8 Hz, 3H), 6.06 (d, J=8.1 Hz, 1H), 5.33 (t, J=8.0 Hz, 1H), 4.57 (m, 1H), 2.99 (m, 1H), 2.48 (s, 3H), 1.68 (m, 1H), 1.57 (m, 1H), 1.38 (m, 1H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe resultant residue was purified by preparative TLC

Sources & evidence

ORD record
ord-e9f0784a074542d1b65b5db9c0e94768
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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