Sodium borohydride → 6-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-pyrrolidin-1-ylbenzonitrile

HRID 1499921Notes

Reaction equation

HRID 1499921 reaction equation
[C:1]([C:4]1[CH:11]=[C:10]([Cl:12])[C:7]([C:8]#[N:9])=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]=1[O:18][CH2:19][CH3:20])(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[Cl:12][C:10]1[C:7]([C:8]#[N:9])=[C:6]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[C:5]([O:18][CH2:19][CH3:20])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:11]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866778384-Acetyl-6-chloro-3-ethoxy-2-pyrrolidin-1-ylbenzonitrile

Product 1

HCID 866778396-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-pyrrolidin-1-ylbenzonitrileYield 101.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 4-acetyl-6-chloro-3-ethoxy-2-pyrrolidin-1-ylbenzonitrile (0.045 g, 0.15 mmol) was dissolved in methanol (3 mL) and cooled in an ice bath. The sodium tetrahydroborate (0.0058 g, 0.15 mmol) was added and the reaction was monitored by LC/MS. After stirring for 1 h, the reaction was taken up in ethyl acetate and washed with water, sodium bicarbonate, brine and dried over magnesium sulfate to give crude 6-chloro-3-ethoxy-4-(1-hydroxyethyl)-2-pyrrolidin-1-ylbenzonitrile as a clear oil (0.045 g, 100%). LCMS calculated for C15H20ClN2O2(M+H)+: m/z=295.1; found 295.1.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with water, sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-5ef09705cc1f48f59ba7db685d706ba6
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…