Water → Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate

HRID 626837Notes

Reaction equation

HRID 626837 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]([C:23]#[N:24])=[C:6]([Cl:25])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[Cl:25][C:6]1[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]=1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86697528Tert-butyl [2-(6-acetyl-4-chloro-3-cyano-2-vinylphenoxy)ethyl]carbamate

Product 1

HCID 86697529Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl [2-(6-acetyl-4-chloro-3-cyano-2-vinylphenoxy)ethyl]carbamate (1.6 g, 4.4 mmol) was dissolved in methanol (40 mL) cooled in an ice bath and the sodium tetrahydroborate (0.16 g, 4.4 mmol) was added. The reaction was stirred for 1 h and water was added to quench residual hydride and the reaction was concentrated to remove the methanol. The aqueous was diluted with ethyl acetate washed with brine, dried over magnesium sulfate and concentrated to give tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate as a glass (1.6 g, 100%). LCMS calculated for C18H23ClN2O4Na (M+Na)+: m/z=389.1; found: 389.1.

Workup

  1. temperaturecooled in an ice bath
  2. customto quench residual hydride
  3. concentrationthe reaction was concentrated
  4. customto remove the methanol
  5. additionThe aqueous was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-985d1c5a7ed945d7bca61e995a8354a8
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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