Aluminium lithium hydride → HCID 86705562, compound

HRID 2279575Notes

Reaction equation

HRID 2279575 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:10][C:11](OC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:23][CH:22]([F:24])[O:21][C:18]1[CH:17]=[CH:16][C:15]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][OH:12])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86705561HCID 86705561, compound

Product 1

HCID 86705562HCID 86705562, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 384 (7.1 g, 20.6 mmol) in THF (150 mL) at −78° C. was added dropwise 1M LiAlH4 (30.8 mL, 30.8 mmol) and stirring was continued for 3 to 4 h. The mixture was diluted with THF, quenched by portion-wise addition of Na2SO4 decahydrate and filtered. Solids were rinsed with additional THF, and the filtrate concentrated. The crude product was purified by SiO2 chromatography eluting with 50% EtOAc/hexanes to afford 3.58 g (55%) of (R)-tert-butyl 1-(4-(difluoromethoxy)phenyl)-3-hydroxypropylcarbamate (386) as a clear viscous liquid which was ca. 95% ee by chiral HPLC.

Workup

  1. customquenched by portion-wise addition of Na2SO4 decahydrate
  2. filtrationfiltered
  3. washSolids were rinsed with additional THF
  4. concentrationthe filtrate concentrated
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-74304f0d9ea746dcb9d2df6e895e8770
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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