Lithium Hydroxide → HCID 44624272, compound

HRID 2040554Notes

Reaction equation

HRID 2040554 reaction equation
[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][C:15]4[CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:21][CH2:22][C:14]=4[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Li+].[OH-]>O1CCOCC1>[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][C:15]4[CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][CH2:22][C:14]=4[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67220437HCID 67220437, compound

Product 1

HCID 44624272HCID 44624272, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the stirred solution of ethyl 2-(7-(4-(methylsulfonyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (40 mg, 0.094 mmol) in dioxane was added 1M LiOH aqueous solution (0.47 mL, 0.47 mmol). The reaction mixture was stirred at room temperature for 24 h. The solvent was partly removed, diluted with water, and acidified with HCl solution. The pinkish solid was collected and dried to give the title compound (26 mg). LCMS m/z=400.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.04-2.08 (m, 1H), 2.35 (dd, J=16.0 and 9.0 Hz, 1H), 2.63-2.75 (m, 4H), 3.20 (s, 3H), 3.45-3.50 (m, 1H), 5.21 (s, 2H), 6.73 (dd, J=8.7 and 2.4 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 7.20 (d, J=8.7 Hz, 1H), 7.71 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.3 Hz, 2H), 10.47 (s, 1H), 12.18 (s, 1H).

Workup

  1. customThe solvent was partly removed
  2. additiondiluted with water
  3. customThe pinkish solid was collected
  4. customdried

Sources & evidence

ORD record
ord-ef6e5e7d5a594d1481595533ba5e8e4c
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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