Lithium borohydride → {4-Iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-3-yl}-methanol
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([I:11])=[CH:9][N:8]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:7]=1)=O)C.[BH4-].[Li+]>C1COCC1>[I:11][C:10]1[C:6]([CH2:4][OH:3])=[N:7][N:8]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of Intermediate 74c (1.22 g, 3.09 mmol) in dry THF (12 mL) was treated with lithium borohydride (0.10 g, 4.64 mmol) and the mixture was stirred at 60° C. for 5 h then stood at RT overnight. The mixture was stirred at 60° C. for a further 5 h then cautiously quenched with water and diluted with EtOAc and water. The phases were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-100% EtOAc in cyclohexane, to give the title compound as a colorless oil (0.68 g, 62%). LCMS (Method 3): Rt 2.89 min, m/z 375 [M+Na+].
Workup
- waitthen stood at RT overnight
- stirringThe mixture was stirred at 60° C. for a further 5 h
- customthen cautiously quenched with water
- additiondiluted with EtOAc and water
- customThe phases were separated
- extractionthe aqueous layer was extracted with EtOAc (2×)
- washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated in vacuo
- customThe residue was purified by FCC
Sources & evidence
- ORD record
- ord-bc334a2f01044ec5aeac044726ba0399
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440974B2
Reaction notes
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