Water → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

HRID 220895Notes

Reaction equation

HRID 220895 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(2-Carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 3.9 mmol, according to the procedure described in J. Med. Chem., 41(14), 2492, 1998) was dissolved in THF (50 ml) and cooled down to 0° C. 2M Borane solution in THF (3.9 ml, 7.8 mmol) was added slowly and the mixture was stirred for 20 h at room temperature. Water was added and solvents were concentrated in vacuo. The residue was dissolved in EtOAC, basified with NaHCO3, washed with brine, dried and concentrated in vacuo to yield the title compound (938 mg, 99%).

Workup

  1. concentrationsolvents were concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAC
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96f953d2d88b4bf29ee9ca51866ad082
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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