Aluminium lithium hydride → (2R,3R)-2-(Allyloxy)-3-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)-methyl)butane-1,4-diol

HRID 73484Notes

Reaction equation

HRID 73484 reaction equation
[CH2:1]([O:4][C@H:5]([C@H:12]([CH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([N:27]2[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]2[CH3:33])[N:21]=1)[C:13](OC(C)C)=[O:14])[C:6](OC(C)C)=[O:7])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:4][C@H:5]([C@H:12]([CH2:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([N:27]2[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]2[CH3:33])[N:21]=1)[CH2:13][OH:14])[CH2:6][OH:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89419083(2R,3S)-Diisopropyl 2-(allyloxy)-3-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)succinate

Product 1

HCID 59582523(2R,3R)-2-(Allyloxy)-3-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)-methyl)butane-1,4-diolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10 (300 mg, 0.70 mmol) in THF (15 mL) at 0° C. was added LiAlH4 (55 mg, 1.4 mmol) in several portions. The reaction mixture was allowed to stir at 0° C. for 20 min then carefully quenched with H2O (50 μL). The solvent was removed by rotary evaporation, and the crude product was purified by flash column chromatography (EtOAc/hexanes, 1:2-1:1) to give 11 (205 mg, 0.60 mmol, 86%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 2.10 (s, 6H), 2.30-2.38 (br s, 1H), 2.39 (s, 3H), 2.83-2.88 (dd, J=4.0, 13.5 Hz, 1H), 2.90-2.94 (dd, J=5.5, 14.0 Hz, 1H), 3.40-3.57 (m, 3H), 3.62-3.67 (m, 2H), 3.74-3.78 (dd, J=5.0, 11.5 Hz, 1H), 4.00-4.04 (dd, J=6.0, 12.5 Hz, 1H), 4.10-4.15 (dd, J=5.0, 13.5 Hz, 1H), 5.15-5.18 (dd, J=1.5, 11.5 Hz, 1H), 5.24-5.28 (dd, J=1.5, 17.5 Hz, 1H), 6.88 (s, 1H), 7.05 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.3, 14.4, 21.2, 21.3, 36.0, 43.0, 60.6, 61.8, 61.9, 71.5, 77.1, 77.3, 77.6, 81.5, 106.9, 117.4, 120.9, 124.0, 128.7, 135.0, 150.5, 151.7, 160.3, 171.4; LCQ-MS (M+H+) calcd for C20H29N2O3 345. found 345; LC-TOF-MS (M+H+) calcd for C20H29N2O3 345.21782. found 345.21772.

Workup

  1. customthen carefully quenched with H2O (50 μL)
  2. customThe solvent was removed by rotary evaporation
  3. customthe crude product was purified by flash column chromatography (EtOAc/hexanes, 1:2-1:1)

Sources & evidence

ORD record
ord-9f72ca478ca34a45ab5602c2c1bc7169
Source dataset
uspto-grants-2014_09
Patent number
US08829187B1

Reaction notes

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