Tetrahydrofuran → HCID 59161539, compound

HRID 221975Notes

Reaction equation

HRID 221975 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12][C:11]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:10]2)=[CH:5][CH:4]=1)#N.C([Mg]Cl)(C)C.[CH2:30]([Mg]Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[NH4+].C1C[O:44]CC1>>[C:31]1([CH2:30][C:1]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12][C:11]4([O:16][CH2:15][CH2:14][O:13]4)[CH2:10]3)=[CH:5][CH:4]=2)=[O:44])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 70864945Tert-butyl [2-(4-cyanophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]carbamateHCID 178418336HCID 178418336, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59161539HCID 59161539, compound

Procedure

To a solution of tert-butyl [2-(4-cyanophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]carbamate (1-6) (15.0 g, 45.4 mmol) in THF (150 mL) at −78° C. was added isopropylmagnesium chloride (22.7 mL, 45.4 mmol, 2M in THF). After 1 hour, benzylmagnesium chloride (68 mL, 135 mmol, 2M in THF) was added and the reaction was allowed to slowly warm to rt over 5 hours. The reaction mixture was poured into saturated ammonium chloride, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-60% EtOAc/Hexane. The appropriate fractions were combined and the solvent removed in vacuo to give tert-butyl {2-[4-(phenylacetyl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-7). MS (M+H)+: 424.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography
  6. washeluting with 1-60% EtOAc/Hexane
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ce036d4030584828bd38c133051de5d2
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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