Potassium Sodium Tartrate → HCID 69810729, compound

HRID 529082Notes

Reaction equation

HRID 529082 reaction equation
C([O:3][C:4](=O)[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.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[OH:3][CH2:4][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])([CH3:24])[CH3:25])=[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

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 68759835HCID 68759835, compound

Product 1

HCID 69810729HCID 69810729, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred 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 (0.039 g, 0.0770 mmol) in THF (0.4 mL) was added dropwise DIBAL-H (0.308 ml, 0.308 mmol) (1M in THF) at 0° C. under nitrogen. The reaction was stirred with warming to about room temperature for 1 hour. The reaction mixture was added dropwise to a saturated solution of Rochelle's salt (6 mL) and stirred overnight. The reaction was extracted with EtOAc (×3). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to yield (R)-tert-butyl 5-(2-hydroxyethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.021 g, 59%). LCMS (APCI+) m/z 465 [M+H]+; Rt=3.39 min.

Workup

  1. temperaturewith warming to about room temperature for 1 hour
  2. stirringstirred overnight
  3. extractionThe reaction was extracted with EtOAc (×3)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f360c279d7eb400ab8af2fa30b354610
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

Loading…