Water → HCID 178453954, compound

HRID 1007291Notes

Reaction equation

HRID 1007291 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1)=O.O>C(OCC)C>[C:21]([O:20][C:18]([NH:17][C@H:14]1[CH2:13][CH2:12][C@@H:11]([CH2:9][OH:8])[CH2:16][CH2:15]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 178501238HCID 178501238, compound

Product 1

HCID 178453954HCID 178453954, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under argon atmosphere, a suspension of 1.29 g of lithium aluminum hydride in 40 mL of anhydrous ethyl ether was treated dropwise with a solution of 5.80 g of cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid methyl ester in 20 mL of anhydrous ethyl ether with cooling in ice, and stirred for 3 hours while allowing to gradually warm to room temperature. The reaction solution was cooled to 0° C., combined a small amount of water to decompose an excessive lithium aluminum hydride. The insolubles were filtered off through Celite, and the filtrate was concentrated, and then the residue was washed with n-hexane to obtain 3.60 g of the desirable compound as colorless crystals.

Workup

  1. temperaturewith cooling in ice
  2. temperatureThe reaction solution was cooled to 0° C.
  3. filtrationThe insolubles were filtered off through Celite
  4. concentrationthe filtrate was concentrated
  5. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-855e1c1293234cbb8c7483a5cb3e7514
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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