HCID 15058610, compound → HCID 80698473, compound

HRID 711011Notes

Reaction equation

HRID 711011 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14]>>[F:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14]

Participants

3

Reactant 2

HCID 15058610HCID 15058610, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 80698473HCID 80698473, compound

Conditions

Temperature
0 °C

Procedure

LiAlH4 (3.4 mL, 2M solution in THF) was added to a solution of compound 135 (114 mg, 0.69 mmol) at 0° C. and then the mixture was brought to room temperature and stirred for 4.5 h. After completion of reaction, the reaction mixture was cooled to 0° C. and carefully quenched the reaction with a saturated solution of potassium-sodium tartarate tetrahydrate by dropwise addition. The reaction mixture was filtered on a Celite bed and the filtrate was dried (Na2SO4) filtered and evaporated. The residue was purified on flash silica gel column chromatography (CH2Cl2:MeOH:NH4OH=25:1:0.1) to yield the compound 136a (which was contaminated minor amount of fluorine reduced product), yield 86 mg (74%) as a colorless syrup. 1H NMR (CD3OD, 300 MHz) δ 7.19-7.25 (m, 2H), 6.87-6.97 (m, 2H), 4.66-4.69 (m, 1H), 4.29-4.32 (m, 1H), 4.20-4.22 (m, 1H), 4.02-4.11 (m, 1H), 3.75-3.79 (m, 2H). HRMS calculated for C9H13NOF (M+H)+: 170.0981. found 170.0982. Compound 136b was prepared in a similar manner.

Workup

  1. customwas brought to room temperature
  2. customAfter completion of reaction
  3. customcarefully quenched
  4. customthe reaction with a saturated solution of potassium-sodium tartarate tetrahydrate
  5. additionby dropwise addition
  6. filtrationThe reaction mixture was filtered on a Celite bed
  7. dry with materialthe filtrate was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on flash silica gel column chromatography (CH2Cl2:MeOH:NH4OH=25:1:0.1)

Sources & evidence

ORD record
ord-3a47b65cdc224c94b6a41620d264e37a
Source dataset
uspto-grants-2015_11
Patent number
US09181253B2

Reaction notes

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