Sodium borohydride → HCID 69812189, compound

HRID 529078Notes

Reaction equation

HRID 529078 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[CH2:14][N:13]([C:28]3[C:29]4[C@H:36]([CH3:37])[CH2:35][CH2:34][C:30]=4[N:31]=[CH:32][N:33]=3)[C:10]2=[CH:11][CH:12]=1)=[O:6].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C:7]2[CH:8]=[C:9]3[C:15]4([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]4)[CH2:14][N:13]([C:28]4[C:29]5[C@H:36]([CH3:37])[CH2:35][CH2:34][C:30]=5[N:31]=[CH:32][N:33]=4)[C:10]3=[CH:11][CH:12]=2)[CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68762560HCID 68762560, compound

Product 1

HCID 69812189HCID 69812189, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-tert-butyl 5-(3-fluorobenzoyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.047 g, 0.087 mmol) in MeOH (0.5 mL) was added NaBH4 (0.0036 g, 0.095 mmol) at about 0° C. The reaction was stirred for 1.5 hours and quenched by the addition of saturated NH4Cl solution. The solvent was evaporated under reduced pressure. The solid was dissolved in water and extracted with EtOAc. The combined extracts were washed with brine, dried MgSO4, filtered and concentrated. The crude residue was purified by column chromatography (1-3% MeOH/DCM) to yield tert-butyl 5-((3-fluorophenyl)(hydroxy)methyl)-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.035 g, 74%). LCMS (APCI+) m/z 545.3 [M+H]+; Rt=4.02 min.

Workup

  1. customquenched by the addition of saturated NH4Cl solution
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe solid was dissolved in water
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine, dried MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by column chromatography (1-3% MeOH/DCM)

Sources & evidence

ORD record
ord-58a669554a264ec9b6b4d941f326fe7a
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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