Benzyl Bromide → HCID 86691267, compound

HRID 2037291Notes

Reaction equation

HRID 2037291 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:19][C:20]([NH:22][C@@:23]1([C:34]([OH:36])=[O:35])[CH2:30][C:27]2([CH2:29][CH2:28]2)[C@@H:26]2[C@H:24]1[C@H:25]2[C:31]([OH:33])=[O:32])=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[C:15]([O:19][C:20]([NH:22][C@@:23]1([C:34]([O:36][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:35])[CH2:30][C:27]2([CH2:29][CH2:28]2)[C@@H:26]2[C@H:24]1[C@H:25]2[C:31]([O:33][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:32])=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86691265HCID 86691265, compound

Product 1

HCID 86691267HCID 86691267, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add cesium carbonate (0.24 g, 730.7 μmol) and benzyl bromide (87.16 μL, 730.7 μmol) to a solution of (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylic acid (0.09 g, 292.29 μmol) in N,N-dimethylformamide (2 mL). Stir at room temperature for 1.5 hours under nitrogen. Quench with water and extract with ethyl acetate. Separate the layers and filter the organics through a hydrophobic frit before concentrating to dryness to yield the crude product (134 mg). Purify by flash chromatography eluting with ethyl acetate:iso-hexane (1:99 to 25:75) to give a clear oil. Purify further by flash chromatography eluting with ethyl acetate:iso-hexane (1:99 10:90) to yield the title product (105 mg, 68%) as a clear oil. MS (m/z): 514 (M+23).

Workup

  1. customQuench with water
  2. extractionextract with ethyl acetate
  3. customSeparate the layers
  4. filtrationfilter the organics through a hydrophobic frit
  5. concentrationbefore concentrating to dryness
  6. customto yield the crude product (134 mg)
  7. customPurify by flash chromatography
  8. washeluting with ethyl acetate:iso-hexane (1:99 to 25:75)
  9. customto give a clear oil
  10. customPurify further by flash chromatography
  11. washeluting with ethyl acetate:iso-hexane (1:99 10:90)

Sources & evidence

ORD record
ord-8b57f5afd27a4a4f86f5b578fb87f61b
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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