Aluminium lithium hydride → HCID 46865943, compound

HRID 473943Notes

Reaction equation

HRID 473943 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C@@H:24]([N:26]3[CH2:31][CH2:30][C@:29]([CH2:38][C:39]([OH:42])([CH3:41])[CH3:40])([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:28][C:27]3=[O:43])[CH3:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>O1CCCC1>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C@@H:24]([N:26]3[CH2:31][CH2:30][C@:29]([CH2:38][C:39]([OH:42])([CH3:40])[CH3:41])([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[O:28][C:27]3=[O:43])[CH3:25])=[CH:22][CH:23]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 58564207HCID 58564207, compound

Product 1

HCID 46865943HCID 46865943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

1 M solution of LiAlH4 in tetrahydrofuran (0.15 mL) was added to a solution of (4′-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-biphenyl-4-yloxy)-acetic acid methyl ester (125 mg) in tetrahydrofuran (2 mL) cooled to −10° C. under argon atmosphere. The resulting mixture was stirred at −10° C. for 2 h and at room temperature for 1 h, before another portion of LiAlH4 (1 M solution in tetrahydrofuran, 0.04 mL) was added at −10° C. The cooling bath was removed and the solution was stirred at room temperature for another 4 h. Then, water was added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by HPLC on reversed phase (acetonitrile/water) to give the title compound.

Workup

  1. additionwas added at −10° C
  2. customThe cooling bath was removed
  3. additionThen, water was added
  4. extractionthe resulting mixture extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by HPLC on reversed phase (acetonitrile/water)

Sources & evidence

ORD record
ord-b552ec3cce4b4c5ba639dd5e02b059d2
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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