Ammonium Chloride → HCID 86675612, compound

HRID 2170041Notes

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

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]-amide (2.91 g, 72%) as a colorless powder. Diastereomeric excess >95% based on 1H NMR.

Workup

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

Sources & evidence

ORD record: ord-fcc13344b4f149a1a88fd627030c8af9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050327B2

Reaction notes

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