Aluminium lithium hydride → (2-Tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methanol

HRID 2175422Notes

Reaction equation

HRID 2175422 reaction equation
[C:1]([O:5][CH:6]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)[CH:7]1[C:16](OCC)=[O:17])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Al+3].[Li+]>C1COCC1>[C:1]([O:5][CH:6]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)[CH:7]1[CH2:16][OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71271320Ethyl 2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropanecarboxylate

Product 1

HCID 71271332(2-Tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropyl)methanolYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of ethyl 2-tert-butoxy-3-(5-methylpyridin-2-yl)cyclopropanecarboxylate (12-4) (350 mg, 1.26 mmol) in THF (2 mL) was cooled to 0° C. Then lithium aluminium tetrahydride (72 mg, 1.89 mmol) was added to the solution at 0° C. and it was stirred for 30 min before restored to the room temperature for 1 h. The reaction was quenched in sequence with 0.1 mL water, 0.05 mL 15% NaOH aqueous, 0.1 mL water. The resulting mixture was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by Pre-TLC (PE/EA=1/1). The product was obtained as a white solid (200 mg, 68%). 1H NMR (400 MHz, MeOD) δ 8.24 (s, 1H), 7.55 (dd, J=8.2, 1.7 Hz, 1H), 7.11 (d, J=8.2 Hz, 1H), 3.66-3.58 (m, 3H), 2.33 (s, 3H), 2.13 (t, J=6.6 Hz, 1H), 1.80 (dd, J=6.4, 3.7 Hz, 1H), 1.06 (s, 9H); LRMS (ES) calculated M+H for C14H22NO2: 236.3. Found: 236.2.

Workup

  1. waitbefore restored to the room temperature for 1 h
  2. customThe reaction was quenched in sequence with 0.1 mL water, 0.05 mL 15% NaOH aqueous, 0.1 mL water
  3. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by Pre-TLC (PE/EA=1/1)

Sources & evidence

ORD record
ord-fe27eacca168403288559c019c635a17
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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