Sodium hydride → HCID 58109416, compound

HRID 2037464Notes

Reaction equation

HRID 2037464 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH:15]([CH2:17][C:18]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(O)[CH2:19][CH:20]=[CH2:21])[CH3:16])[C:11](=[O:14])[O:12]C)[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+]>>[CH2:19]([C:18]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[O:14][C:11](=[O:12])[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH3:9])[CH:15]([CH3:16])[CH2:17]1)[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 58109231HCID 58109231, compound

Product 1

HCID 58109416HCID 58109416, compound

Procedure

To a solution of methyl (S)-1-(4-bromophenyl)ethyl(4-(4-fluorophenyl)-4-hydroxyhept-6-en-2-yl)carbamate (20 mg, 0.043 mmol) was added NaH at 0° C. The mixture was stirred and heated to reflux for 1 h. The mixture was cooled to rt and quenched with water. The organic phase was extracted by EtOAc and concentrated to give the crude product which was purified by preparative TLC to give three isomers of 6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-4-methyl-1,3-oxazinan-2-one.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. customquenched with water
  4. extractionThe organic phase was extracted by EtOAc
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-cf9f61c70b8044349b5a7224e1d0d229
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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