Lithium Hydroxide → HCID 66904958, compound

HRID 1692090Notes

Reaction equation

HRID 1692090 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@@H:18]3[CH2:22][CH2:21][N:20]([N:23]4[CH2:28][CH2:27][CH:26]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:25][CH2:24]4)[C:19]3=[O:40])=[C:13]([Cl:41])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1>[Cl:41][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH:16]=[CH:15][C:14]=1[CH2:17][C@@H:18]1[CH2:22][CH2:21][N:20]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][Si:30]([CH:31]([CH3:32])[CH3:33])([CH:34]([CH3:36])[CH3:35])[CH:37]([CH3:39])[CH3:38])[CH2:25][CH2:24]2)[C:19]1=[O:40]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66905158HCID 66905158, compound

Product 1

HCID 66904958HCID 66904958, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 3′-Chloro-4′-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (0.76 g) in THF (15 mL) with 2N LiOH (15 mL) at room temperature for 5 hours. Partition the mixture between ethyl acetate (25 mL) and 1 N HCl (10 mL). Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford 0.73 g (98%) of the title compound. MS (m/z): 585 (M+).

Workup

  1. customPartition the mixture between ethyl acetate (25 mL) and 1 N HCl (10 mL)
  2. dry with materialDry the organic layer with Na2SO4
  3. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-960abd2787504943a2b9620ba0055d8c
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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