Sodium borohydride → HCID 67470570, compound

HRID 407939Notes

Reaction equation

HRID 407939 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][CH2:19][C@H:18]([NH:22][C:23]4[CH:28]=[C:27]([F:29])[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][C:24]=4[F:34])[C:17]3=[O:35])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[F:34][C:24]1[CH:25]=[C:26]([S:30]([CH3:33])(=[O:31])=[O:32])[C:27]([F:29])=[CH:28][C:23]=1[NH:22][C@H:18]1[CH2:19][CH2:20][CH2:21][N:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][N:8]=3)[CH2:11][CH2:12]2)[C:17]1=[O:35]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67470532(S)-1'-(5-acetylpyridin-2-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4'-bipiperidin-2-one

Product 1

HCID 67470570HCID 67470570, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1′-(5-acetylpyridin-2-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one (0.310 g, 0.612 mmol) was dissolved in methanol (5 mL). NaBH4 (0.0232 g, 0.612 mmol) was added slowly and stirred at ambient temperature for 1 hour. The reaction was concentrated and purified over silica gel (50-100% EtOAc in hexanes) to afford (3S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1′-(5-(1-hydroxyethyl)pyridin-2-yl)-1,4′-bipiperidin-2-one (0.265 g, 0.469 mmol, 76.6% yield). Mass spectrum (apci) m/z=509.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified over silica gel (50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c56e84e6f8b2419e91f40402e3f77003
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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