1-N-Boc-4-Piperidinecarboxylic acid methyl ester → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 2059912Notes

Reaction equation

HRID 2059912 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH:4]([C:7](OC)=[O:8])[CH2:3][CH2:2]1.[Li+].[BH4-]>C1COCC1>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 4148881Lithium borohydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (171.3 mmol, 1 eq) in THF (250 ml) was added LiBH4 (342.6 mmol, 2 eq) at 0° C. The reaction mixture was then heated at reflux for 2 h and then cooled to 0° C. Ice-water (100 g) was added and the aqueous layer was extracted with ethyl acetate (200 ml). The organic layer was washed with brine (50 ml), the layers were separated, and the organics dried over Na2SO4, concentrated and employed in the next step without further purification. Yield: 82%

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 2 h
  3. extractionthe aqueous layer was extracted with ethyl acetate (200 ml)
  4. washThe organic layer was washed with brine (50 ml)
  5. customthe layers were separated
  6. dry with materialthe organics dried over Na2SO4
  7. concentrationconcentrated
  8. customemployed in the next step without further purification

Sources & evidence

ORD record
ord-49ad721b26644447b00c8ce7ec7e2176
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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