Ammonium Chloride → HCID 71003680, compound

HRID 2272657Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)=[O:7].[CH3:17][Mg]Br.[Cl-].[NH4+]>C1COCC1>[OH:7][C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (1S,3R)-methyl 3-(thiazole-2-carbonyl)cyclopentanecarboxylate (148 mg, 1.75 mmol) in THF (6 mL) and at −78° C. was added methylmagnesium bromide (582 mL, 1.75 mmol), the solution was stirred at −78° C. for 30 minutes. Saturated aqueous ammonium chloride was added and the mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc, organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was absorbed on silica and purified by flash chromatography to afford (1S,3R)-methyl 3-(1-hydroxy-1-(thiazol-2-yl)ethyl)cyclopentanecarboxylate. MS ESI calc'd. for C12H18NO3S [M+H]+ 256. found 256. 1H NMR (500 MHz, DMSO-d6) δ 7.67 (t, J=3.0 Hz, 1H), 7.50 (d, J=3.0 Hz, 1H), 3.58-3.57 (m, 3H), 3.52 (s, 1H), 2.75-2.62 (m, 1H), 2.43-2.35 (m, 1H), 1.97-1.91 (m, 1H), 1.78-1.51 (m, 4H), 1.46-1.44 (m, 3H), 1.25-1.19 (m, 1H).

Workup

temperatureto warm to room temperature
extractionThe mixture was extracted with EtOAc, organic layer
dry with materialwas dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was absorbed on silica
custompurified by flash chromatography

Sources & evidence

ORD record: ord-1d2a40b4ef5f4ebc8dc2f342635b9512
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120785B2

Reaction notes

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