Aluminium lithium hydride → HCID 22124446, compound

HRID 1858112Notes

Reaction equation

HRID 1858112 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]([F:26])([F:25])[C:21](OC)=[O:22])=O)(C)(C)C>>[F:26][C:20]([F:25])([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:14]1[CH3:12])[CH2:21][OH:22]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53758098HCID 53758098, compound

Product 1

HCID 22124446HCID 22124446, compoundYield 64.6%

Procedure

To a solution of 2-(difluoro-methoxycarbonylmethyl)piperidine-1-carboxylic acid tert-butyl ester (1.14 g in 30 mL dry diethyl ether) at 0° C. was added 580 mg lithium aluminum hydride and the mixture stirred at low temperature. After 15 minutes, the reaction was quenched by the sequential addition of 0.58 mL water, 0.58 mL 2N sodium hydroxide and 0.74 mL water. The mixture was stirred vigorously for 1 hour then filtered over diatomaceous earth. The filtrate was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15) to give the title compound (450 mg).

Workup

  1. customthe reaction was quenched by the sequential addition of 0.58 mL water, 0.58 mL 2N sodium hydroxide and 0.74 mL water
  2. stirringThe mixture was stirred vigorously for 1 hour
  3. filtrationthen filtered over diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15)

Sources & evidence

ORD record
ord-c652c36e952b40d38d09f777b2590a10
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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