Sodium borohydride → HCID 86601776, compound

HRID 1191950Notes

Reaction equation

HRID 1191950 reaction equation
[CH3:1][C:2]1([N:15]2[CH2:20][CH2:19][N:18]([CH:21]3[C:29]4[C:24](=[CH:25][C:26]([C:30]([F:33])([F:32])[F:31])=[CH:27][CH:28]=4)[C:23](=[O:34])[CH2:22]3)[CH:17]([CH3:35])[CH2:16]2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:34][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[CH:21]([N:18]2[CH2:19][CH2:20][N:15]([C:2]3([CH3:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)[CH2:16][C@@H:17]2[CH3:35])[CH2:22]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68743987HCID 68743987, compound

Product 1

HCID 86601776HCID 86601776, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-methyl-4-{3-methyl-4-[3-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazin-1-yl}piperidine-1-carboxylate (100 mg, 0.202 mmol) in ethanol (7 mL) was added sodium borohydride (57 mg, 1.5 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated in vacuo, and the residue was quenched with 10 mL of 1 N aqueous NaOH solution and 10 mL of EtOAc. The organic phase was separated and the aqueous layer was extracted with EtOAc twice (2×15 mL). The combined extracts were washed with brine, dried over Na2SO4 and evaporated under reduced pressure to give the desired product which was directly used for the next step (93 mg, 92%). LC-MS [M+1]=498.4.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was quenched with 10 mL of 1 N aqueous NaOH solution and 10 mL of EtOAc
  3. customThe organic phase was separated
  4. extractionthe aqueous layer was extracted with EtOAc twice (2×15 mL)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-affb78368cb547b1b9690204be5358f5
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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