Ammonia → HCID 16099062, compound

HRID 1642182Notes

Reaction equation

HRID 1642182 reaction equation
[C:1]1([C@@H:7]([NH:9][C@H:10]2[C@@H:15]([C:16](OCC)=[O:17])[CH2:14][CH2:13][N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N>O1CCCC1>[OH:17][CH2:16][C@@H:15]1[CH2:14][CH2:13][N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:11][C@@H:10]1[NH:9][C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 53629881HCID 53629881, compound

Product 1

HCID 16099062HCID 16099062, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 61B (60.0 g, 0.159 mol) in tetrahydrofuran (200 mL) was added dropwise to a mixture of lithium aluminum hydride (7.00 g, 0.175 mol, 95%) in tetrahydrofuran (300 mL) at 0° C. After the addition was complete, the mixture was allowed to warm to ambient temperature and was quenched by slow addition of Na2SO4.10H2O (excess). The mixture was stirred for 16 hours, filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 50% ethyl acetate/hexanes) to provide two diastereomers, a more mobile diastereomer determined to be the (3S,4S) diastereomer Rf=0.27 in 75% ethyl acetate/hexanes, 15.0 g, 44.8 mmol, 28% yield and a less mobile diastereomer determined to be the (3R,4R) diastereomer (Rf=0.20 in 75% ethyl acetate/hexanes, 22.5 g, 67.3 mmol, 42% yield). MS (DCI/NH3) m/z 335 (M+H)+.

Workup

  1. additionAfter the addition
  2. customwas quenched by slow addition of Na2SO4.10H2O (excess)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (SiO2, 50% ethyl acetate/hexanes)
  6. customto provide two diastereomers

Sources & evidence

ORD record
ord-eac45ed992404b20835e55e5e4dcc777
Source dataset
uspto-grants-2012_02
Patent number
US08119635B2

Reaction notes

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