Aluminium lithium hydride → HCID 25263463, compound

HRID 1375196Notes

Reaction equation

HRID 1375196 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:19](O)=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][C@@H:18]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:19][OH:20])(=[O:15])=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68543369HCID 68543369, compound

Product 1

HCID 25263463HCID 25263463, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of LAH (1.0 M in THF, 1.5 mL, 1.5 mmol) was added dropwise at 0° C. a solution of (αS)-α-[[(4-chlorophenyl)sulfonyl]amino]cyclohexaneacetic acid (0.50 g, 1.507 mmol) in THF (8.0 mL). After the addition was complete, the reaction mixture was allowed to warm to 25° C. After 24 hours, the reaction was quenched by sequential addition of H2O (60 μL), 15% NaOH (60 μL) and H2O (180 μL). The precipitate was filtered and washed with THF. The combined THF solution was evaporated to a clear oil which afforded a white solid after washing with hexane. This white solid was purified by flash chromatography (eluant: 1-1 hexane/ethyl acetate), washed with hexane and pumped on to afford 0.179 g (37%) of the desired product as a white solid, mp 115-118° C. Mass Spectrum (+APCI): 318 ([M+H]+). Anal: Calc'd for C14H20ClNO3S: C, 52.91; H, 6.34; N, 4.41. Found: C, 52.16; H, 6.25; N, 4.40.

Workup

  1. additionAfter the addition
  2. customthe reaction was quenched by sequential addition of H2O (60 μL), 15% NaOH (60 μL) and H2O (180 μL)
  3. filtrationThe precipitate was filtered
  4. washwashed with THF
  5. customThe combined THF solution was evaporated to a clear oil which
  6. customafforded a white solid
  7. washafter washing with hexane
  8. customThis white solid was purified by flash chromatography (eluant: 1-1 hexane/ethyl acetate)
  9. washwashed with hexane

Sources & evidence

ORD record
ord-cb8121e21412471caf1053102d47f533
Source dataset
uspto-grants-2007_01
Patent number
US07166622B2

Reaction notes

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