Tetrahydrofuran → HCID 178472362, compound

HRID 928117Notes

Reaction equation

HRID 928117 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=O)=[N:4][CH:3]=1.C([BH3-])#[N:21].[Na+].C([O-])(=O)C.[NH4+].C1COCC1>CCOC(C)=O.CO>[NH2:21][CH:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178472369HCID 178472369, compound

Product 1

HCID 178472362HCID 178472362, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

trans-Ethyl 4-(5-bromothiazole-2-carbonyl)cyclohexanecarboxylate (150 mg, 0.433 mmol), sodium cyanoborohydride (63 mg, 1.00 mmol), ammonium acetate (83 mg, 1.08 mmol), THF (0.6 mL), and methanol (1.8 mL) were combined in a sealed vial and heated to a temperature of 80° C. for 16 hours. The mixture was cooled to 23° C. and subsequently transferred to a separatory funnel containing EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated to afford crude trans-ethyl 4-(amino(5-bromothiazol-2-yl)methyl)cyclohexanecarboxylate, which was used directly in the subsequent synthetic transformation without purification. MS ESI calc'd. For C13H20BrN2O2S [M+H]+ 347, 349. found 347, 349.

Workup

  1. temperatureThe mixture was cooled to 23° C.
  2. customsubsequently transferred to a separatory funnel
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-899f4aed32784106959a5dc3804c37e5
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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