HCID 20781251, compound → HCID 20781265, compound

HRID 2181268Notes

Reaction equation

HRID 2181268 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[F:39])[CH2:22][CH2:21][CH:20]([NH:23][S:24]([CH2:27][C:28](OC)=[O:29])(=[O:26])=[O:25])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[F:39])[CH2:18][CH2:19][CH:20]([NH:23][S:24]([CH2:27][CH2:28][OH:29])(=[O:26])=[O:25])[CH2:21][CH2:22]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 20781251HCID 20781251, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20781265HCID 20781265, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (0.29 ml of 1M solution in tetrahydrofuran, 0.29 mmol) in tetrahydrofuran (3 ml) at 0° C. under nitrogen was treated dropwise with a solution of the ester of Example 38 (50 mg, 0.1 mmol) in tetrahydrofuran (9 ml). The reaction mixture was stirred at ambient temperature for 3 days, quenched with aqueous sodium sulfate then partitioned between water and ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated to give a residue (47 mg) which was purified using preparative thin layer chromatography eluting with ethyl acetate:hexane 2:1 to give the desired product (12 mg). 1H NMR (CDCl3) 7.38 (2H, d, J=9.2 Hz), 7.32 (2H, d, J=8.8 Hz), 7.08-7.04 (2H, m), 6.88-6.84 (1H, m), 5.39 (1H, d, J=6.4 Hz), 4.51-4.09 (2H, m), 3.65-3.63 (1H, m), 3.28 (2H, t, J=5.2 Hz), 2.83 (1H, t, J=5.6 Hz), 2.56-2.44 (4H, m), 2.05-2.20 (2H, m), 1.57-1.50 (2H, m); M/z(ES−)=492/494

Workup

  1. customquenched with aqueous sodium sulfate
  2. customthen partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3d681269805f440d8c2de21e3d63b464
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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