Diethyl Ether → HCID 69087654, compound

HRID 1046984Notes

Reaction equation

HRID 1046984 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5].[CH3:25][Mg]Br.CCOCC>O1CCCC1>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)(=[O:5])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86664667HCID 86664667, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69087654HCID 69087654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (1-(4-(methoxy(methyl)carbamoyl)phenyl)cyclobutyl)carbamate (0.5 g, 1 eq.) in tetrahydrofuran (THF) (5 mL) cooled to 0° C. was slowly added a 1 M solution of methylmagnesium bromide in ether (4.5 mL, 3 eq.). The reaction mixture was stirred at room temperature overnight then quenched by the addition of saturated aqueous ammonium chloride (15 mL). The mixture was extracted with dichloromethane (2×25 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography (15% ethyl acetate in dichloromethane), giving tert-butyl (1-(4-acetylphenyl)cyclobutyl)carbamate as a colorless oil which solidified upon standing (261 mg, 60%). 1H NMR (DMSO-d6) 400 MHz δ 7.91 (d, J=8.0 Hz, 2H), 7.74 (br. s, 1 H), 7.50 (d, J=8.4 Hz, 2H), 2.56 (s, 3H), 2.45-2.32 (m, 4H), 2.06-1.94 (m, 1H), 1.86-1.75 (m, 1H), 1.33 (s, 9H).

Workup

  1. customthen quenched by the addition of saturated aqueous ammonium chloride (15 mL)
  2. extractionThe mixture was extracted with dichloromethane (2×25 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by column chromatography (15% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-a1d1f61aca584fb1b3641c069a84cd34
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

Loading…