Borane → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1608173Notes

Reaction equation

HRID 1608173 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 15.0 g (65.5 mmole) of the 4-carboxy-piperidine-1-carboxylic acid-t-butyl ester produced above, in 200 ml of dry tetrahydrofuran, under nitrogen gas, was added 98.2 ml (98.2 mmole) of 1.0 M borane in tetrahydrofuran over 10 minutes. The reaction mixture was stirred an additional 4 hours at room temperature, quenched with 500 ml of aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to give 14.1 g of 4-hydroxymethyl-piperidine-1-carboxylic acid t-butyl ester as a white solid with melting point 75°-76° C.

Workup

  1. customquenched with 500 ml of aqueous saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-491c85db93654cbaa83eb065e30ffb13
Source dataset
uspto-grants-1989_09
Patent number
US04870083

Reaction notes

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