HCID 57918267, compound → HCID 59598521, compound

HRID 2266235Notes

Reaction equation

HRID 2266235 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([C:14]([C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)=[O:15])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([C:5]1[O:6][C:7]2[C:13]([C@:14]([C@@H:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)([OH:15])[CH2:10][CH2:8][CH2:9][CH2:5][O:6][CH3:7])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 57918267HCID 57918267, compound

Product 1

HCID 59598521HCID 59598521, compoundYield 195.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL three-necked flask was charged with (R)-tert-butyl 3-(2-tert-butylbenzofuran-7-carbonyl)piperidine-1-carboxylate (0.41 g, 1.08 mmol) and anhydrous THF (8 mL). The flask was evacuated and refilled with N2. The mixture was cooled with dry ice-acetone bath and the Grignard reagent derived from 1-chloro-4-methoxy-butane (5.4 mL, 2M) was added. The reaction mixture was allowed to slowly warm to rt while stirring overnight. The mixture was quenched with satd aq NH4Cl (20 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford (R)tert-butyl 3-((S)-1-(2-tert-butylbenzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (0.5 g, 100%). 1H NMR:(CDCl3): 1.34 (s, 9H), 1.46 (s, 9H), 1.51 (m, 9H), 2.02 (m, 1H), 2.18 (m, 1H), 2.50 (m, 2)H, 2.67 (t, 1H), 3.23 (m, 5H), 3.99 (s, 1H), 4.43 (s, 1H), 6.35 (s, 1H), 7.16 (t, 1H), 7.23 (d, 1H), 7.39 (dd, 1H),

Workup

  1. customThe flask was evacuated
  2. additionrefilled with N2
  3. temperatureThe mixture was cooled with dry ice-acetone bath
  4. additionwas added
  5. customThe mixture was quenched with satd aq NH4Cl (20 mL)
  6. extractionextracted with EtOAc (3×20 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8771bbc49ee4edca8f1b533613e457a
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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