Ammonium Chloride → HCID 86675612, compound

HRID 1908666Notes

Reaction equation

HRID 1908666 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([C:11](=[N:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[NH4+].[Cl-]>C1COCC1>[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:17])[CH3:18])=[O:15])[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 123275310HCID 123275310, compound

Product 1

HCID 86675612HCID 86675612, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-66 °C

Procedure

A round-bottomed flask was charged with (R)-2-methyl-propane-2-sulfinic acid [1-(6-isopropoxy-pyridin-3-yl)-ethylidene]-amide (4.00 g, 14.2 mmol) in THF (50 mL) under N2 and cooled to −66° C. (internal temperature). A 1.00 M solution of L-Selectride in THF (29.0 mL, 29.0 mmol) was added drop wise over 15 minutes. The mixture was stirred at −70° C. for 1 hour. The cold mixture was poured into saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and evaporated to dryness. Flash chromatography (silica, EtOAc) gave (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(6-isopropoxy-pyridin-3-yl)-ethyl]-amid (2.91 g, 72%) as a colorless powder. Diastereomeric excess >95% based on 1H NMR.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8b728efca22e45dfa539de02ef9396b2
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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