Sodium borohydride → HCID 18316371, compound

HRID 276298Notes

Reaction equation

HRID 276298 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[N:16]([CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14][S:13]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[N:16]([CH2:17][CH:18]([OH:23])[C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:15][CH2:14][S:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18316134HCID 18316134, compound

Product 1

HCID 18316371HCID 18316371, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Methyl-4-nitrophenylimino)-1,3-thiazolidine was prepared in a manner analogous to that described in method C2a and was alkylated with 1-bromo-3,3-dimethyl-2-butanone in a manner analogous to that described in Method D2a to give 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-oxobutyl)-1,3-thiazolidine. To a solution of 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-oxobutyl)-1,3-thiazolidine (0.022 g, 0.065 mmol) in MeOH (2 mL) was added NaBH4 (0.0096 g, 0.26 mmol) in portions. The resulting mixture was stirred at room temp for 4 h, then was separated between EtOAc (10 mL) and H2O (5 mL) and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were sequentially washed with H2O (15 mL), a saturated NaCl solution (15 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by preparative TLC (20% EtOAc/hexane) to yield 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-hydroxybutyl)-1,3-thiazolidine (0.024 g, 92%); FAB-MS m/z 338 ((M+H)+).

Workup

  1. customwas separated between EtOAc (10 mL) and H2O (5 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were sequentially washed with H2O (15 mL)
  4. dry with materiala saturated NaCl solution (15 mL), dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative TLC (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-396ae61b6d9e4dec92f8e619ac7f7207
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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