Sodium borohydride → HCID 86732639, compound

HRID 626399Notes

Reaction equation

HRID 626399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]/[S@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])/[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][S@:11]([C:13]([CH3:14])([CH3:16])[CH3:15])=[O:12])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 25023178HCID 25023178, compound

Product 1

HCID 86732639HCID 86732639, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
-50 °C

Procedure

(S,E)-N-(1-(4-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide (0.5 g, 1.66 mmol) was dissolved in THF/H2O=50:1 (10 mL) and cooled to −50° C. Then NaBH4 (0.19 g, 4.97 mmol) was added. The resulting mixture was warmed to RT over 3 h and then concentrated. The residue was purified by column chromatography to afford the titled compound.

Workup

  1. temperatureThe resulting mixture was warmed to RT over 3 h
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e7a872f4e9e54e5787b536c5f8f06122
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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