Sodium Hydroxide → tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 1831805Notes

Reaction equation

HRID 1831805 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:19]#[N:20])([O:14][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:19][NH2:20])([OH:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23396320HCID 23396320, compound

Product 1

HCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Cyano-4-trimethylsilanyloxy-piperidine-1-carboxylic acid tert-butyl ester (7.5 g) was dissolved in 100 ml of tetrahydro-furan under an argon atmosphere. A solution of lithium aluminium hydride in tetrahydro-furan (30 ml, 1 molar) was dropwise added at 0° C. After stirring for 15 hours at room temperature, a sodium hydroxide solution (20%) was slowly added under cooling. The solid was filtered after dilution with ethyl acetate and the organic layer evaporated. The crude material contains a mixture of the desired product (MS: 231.2 (M+H)+) and the corresponding trimethylsiliyl ether (MS: 303.1 (M+H)+) and was used without further purification.

Workup

  1. temperatureunder cooling
  2. filtrationThe solid was filtered after dilution with ethyl acetate
  3. customthe organic layer evaporated
  4. additiona mixture of the desired product (MS: 231.2 (M+H)+)
  5. customthe corresponding trimethylsiliyl ether (MS: 303.1 (M+H)+) and was used without further purification

Sources & evidence

ORD record
ord-5640515c1f784e45bdf80e5bea765115
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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