Diethylamine → [(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester

HRID 503922Notes

Reaction equation

HRID 503922 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:12][OH:13])[CH2:9][C:10]#[N:11])=[C:4]([O:14][CH3:15])[CH:3]=1.[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.[BH4-].[Na+].C(NCC)C>CO>[C:20]([O:19][C:17](=[O:16])[NH:11][CH2:10][CH2:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[O:14][CH3:15])[CH2:12][OH:13])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 90495Di-tert-butyl dicarbonateHCID 4311764Sodium borohydrideHCID 66876540(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile

Product 1

HCID 66877031[(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile (459 mg, 1.699 mmol) in MeOH (12.1 mL) at 0° C. was added (BOC)2O (736.3 mg, 3.398 mmol), NiCl2.6H2O (40.75 mg, 0.17 mmol), and (in portions) sodium borohydride (450.3 mg, 11.9 mmol). The mixture was stirred at room temperature for 18 hours. Diethylamine (0.183 mL, 1.699 mmol) was then added and the mixture was stirred for 30 minutes. Solvent was evaporated under reduced pressure and a solution of aqueous NaHCO3 (10%) was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 405 mg (64% yield) of [(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyl]-carbamic acid tert-butyl ester.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customSolvent was evaporated under reduced pressure
  3. additiona solution of aqueous NaHCO3 (10%) was added
  4. extractionThe mixture was extracted with EtOAc
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

Sources & evidence

ORD record
ord-ee585bb7e2044f63b2ee2f528f81459e
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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