Thionyl Chloride → HCID 68182344, compound

HRID 1624009Notes

Reaction equation

HRID 1624009 reaction equation
[CH2:1]([NH:8][C@@H:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[S:25](Cl)(Cl)=[O:26]>C(Cl)Cl>[C:12]([C@H:9]1[CH2:10][O:11][S:25](=[O:26])[N:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 16655564HCID 16655564, compound

Product 1

HCID 68182344HCID 68182344, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(Benzylamino)-3,3-dimethylbutan-1-ol (5.77 g, 27.8 mmol) in dry DCM (100 mL) was cooled down to −20° C., DIEA (19.39 ml, 111 mmol) was added, followed by thionyl chloride (2.228 ml, 30.6 mmol) in DCM (10 mL). The reaction mixture was stirred for 1 h at this temperature, then concentrated. The residue was purified by column chromatography to give the title compound (6.26 g) as a diastereomeric mixture. LCMS m/z=254.0 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-33d5d2be15c1450ca01afb622fe0f7c3
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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