Sodium borohydride → (Racemic)-1-{1-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanol

HRID 1850351Notes

Reaction equation

HRID 1850351 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([N:21]3[CH2:26][CH2:25][CH:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.[BH4-].[Na+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH:13]([C:15]2[C:16]([N:21]3[CH2:26][CH2:25][CH:24]([CH:27]([OH:29])[CH3:28])[CH2:23][CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 585472291-{1-[3-(1-Quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanone

Product 1

HCID 58546785(Racemic)-1-{1-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-{1-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanone (96.75 mg, 0.25 mmol) in MeOH (10 mL) was added NaBH4 (37 mg, 1 mmol). The mixture was stirred at RT for 2 h. The reaction mixture was concentrated to give the product (racemic)-1-{1-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanol (76 mg, 0.20 mmol, yield 78%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-5aecf2e19b27481b8a1c99c7f9d3ddcc
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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