Lithium hydroxide, monohydrate → HCID 68762168, compound

HRID 529073Notes

Reaction equation

HRID 529073 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][C:6]1[CH:7]=[C:8]2[C:14]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:13][N:12]([C:27]3[C:28]4[C@H:35]([CH3:36])[CH2:34][CH2:33][C:29]=4[N:30]=[CH:31][N:32]=3)[C:9]2=[CH:10][CH:11]=1)C.O[Li].O>C1COCC1.O>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C:14]2([C:8]3[C:9](=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:37])=[O:3])[CH:7]=3)[N:12]([C:27]3[C:28]4[C@H:35]([CH3:36])[CH2:34][CH2:33][C:29]=4[N:30]=[CH:31][N:32]=3)[CH2:13]2)[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68759835HCID 68759835, compound

Product 1

HCID 68762168HCID 68762168, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of (R)-tert-butyl 5-(2-ethoxy-2-oxoethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.325 g, 0.641 mmol) in THF:H2O (2:1, 3 mL) was treated with LiOH—H2O (0.067 g, 1.6 mmol) at about 0° C. The reaction was stirred with warming to about room temperature overnight. The reaction was concentrated and diluted with EtOAc. The organic was washed with saturated NaHCO3, acidified with 1N HCl, and extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to yield (R)-2-(1′-(tert-butoxycarbonyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-5-yl)acetic acid. LCMS (APCI+) m/z 479.3 [M+H]+; Rt=2.82 min.

Workup

  1. temperaturewith warming to about room temperature overnight
  2. concentrationThe reaction was concentrated
  3. additiondiluted with EtOAc
  4. washThe organic was washed with saturated NaHCO3
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a0594cfaa8054438bd91feccb195c85a
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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