Lithium hydroxide, monohydrate → HCID 57659364, compound

HRID 1009816Notes

Reaction equation

HRID 1009816 reaction equation
O[CH2:2][C@@H:3]([N:10]1[C@H:23]2[C@H:13]([CH2:14][C:15]3([C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=42)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH2:12][C:11]1=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[OH-].[Li+]>CS(C)=O>[C:4]1([C:3]([N:10]2[C@H:23]3[C@H:13]([CH2:14][C:15]4([C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=53)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[CH2:12][C:11]2=[O:28])=[CH2:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57659367HCID 57659367, compound

Product 1

HCID 57659364HCID 57659364, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (3aR,9bS)-1-((S)-2-hydroxy-1-phenylethyl)-1,3a,4,9b-tetrahydrospiro[benzo[g]indole-5,4′-piperidin]-2(3H)-one (Step 4, 2.3 g, 6.1 mmol) and lithium hydroxide monohydrate (2.3 g, 55 mmol) in DMSO (15 ml) was heated at 170° C. for 4 h. The reaction mixture was evaporated. The residue was poured into water, extracted with EtOAc (3×). The extracts were concentrated to give the title compound as brown oil (1.5 g).

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe residue was poured into water
  3. extractionextracted with EtOAc (3×)
  4. concentrationThe extracts were concentrated

Sources & evidence

ORD record
ord-41ea55f4600049648454fcd2a83e6c6e
Source dataset
uspto-grants-2011_07
Patent number
US07973162B2

Reaction notes

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