tert-butyl (3S)-3-{[1'-(diphenylmethyl)-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indol]-6-yl]oxy}pyrrolidine-1-carboxylate → tert-butyl (3S)-3-[(2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indol]-6-yl)oxy]pyrrolidine-1-carboxylate

HRID 2385205Notes

Reaction equation

HRID 2385205 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[CH:22][C:23]([O:25][C@H:26]5[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]5)=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:38])C=CC=CC=1>CO>[O:38]=[C:9]1[C:10]2([C:20]3[CH:21]=[CH:22][C:23]([O:25][C@H:26]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]4)=[CH:24][C:19]=3[O:18][CH2:17]2)[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8]1

Participants

3

Reactant 1

HCID 59352336tert-butyl (3S)-3-{[1'-(diphenylmethyl)-2'-oxo-1,2'-dihydrospiro[1-benzofuran-3,3'-indol]-6-yl]oxy}pyrrolidine-1-carboxylate

Product 1

HCID 59352722tert-butyl (3S)-3-[(2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indol]-6-yl)oxy]pyrrolidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of tert-butyl (3S)-3-{[1′-(diphenylmethyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl]oxy}pyrrolidine-1-carboxylate (0.50 g, 0.85 mmol) in methanol (20 mL) was degassed by bubbling through nitrogen for one hour before palladium hydroxide on carbon (20%, 0.084 g) was added. The mixture was stirred under 120 psi hydrogen at 60° C. for 48 h. The mixture was filtered through a pad of celite, the filtrate was concentrated in vacuo. The obtained residue was recrystallized from ethyl acetate and hexanes to afford tert-butyl (3S)-3-[(2′-oxo-1,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl)oxy]pyrrolidine-1-carboxylate (0.25 g, 70%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.01 (br s, 1H), 7.29-7.09 (m, 1H), 7.12 (d, J=7.0 Hz, 1H), 7.02 (dd, J=7.5, 0.8 Hz, 1H), 6.92 (d, J=7.7 Hz, 1H), 6.66 (d, J=8.3 Hz, 1H), 6.47 (d, J=2.1 Hz, 1H), 6.33 (dd, J=8.3, 2.1 Hz, 1H), 4.96 (d, J=9.1 Hz, 1H), 4.81 (s, 1H), 4.69 (d, J=9.1 Hz, 1H), 3.64-3.37 (m, 4H), 2.22-1.96 (m, 2H), 1.45 (s, 9H); MS (ES+) m/z 445.0 (M+23).

Workup

  1. customwas degassed
  2. customby bubbling through nitrogen for one hour before palladium hydroxide on carbon (20%, 0.084 g)
  3. additionwas added
  4. filtrationThe mixture was filtered through a pad of celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe obtained residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-1682a456027e4321b7ebc036c8a8ceae
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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