Lithium borohydride → HCID 21914755, compound

HRID 1246433Notes

Reaction equation

HRID 1246433 reaction equation
[C:1]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12](OCC)=[O:13])[N:11]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[BH4-].[Li+]>O1CCCC1>[OH:13][CH2:12][C:10]1[N:11]=[C:7]([NH:6][C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 21914754HCID 21914754, compound

Product 1

HCID 21914755HCID 21914755, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of ethyl 2-(isobutyrylamino)-1,3-thiazole-4-carboxylate (1.4 g) and tetrahydrofuran (28 ml) was added lithium borohydride (252 mg) portionwise, and the mixture was refluxed for 6 hours. The reaction mixture was cooled to 0° C., quenched with methanol (5 ml) and concentrated in vacuo. The residue was suspended with 10% methanol/chloroform (100 ml), and the insoluble materials were filtered off. The filtrate was purified by flash column chromatography on silica-gel with 5% methanol/chloroform as an eluent. The crystalline residue was collected and washed with diisopropyl ether to give N-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-2-methylpropanamide (1.0 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customquenched with methanol (5 ml)
  3. concentrationconcentrated in vacuo
  4. filtrationthe insoluble materials were filtered off
  5. customThe filtrate was purified by flash column chromatography on silica-gel with 5% methanol/chloroform as an eluent
  6. customThe crystalline residue was collected
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-7d48de3b083b412c91e0ba4c3950016f
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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