1-Bromo-2-propanol → tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

HRID 1257745Notes

Reaction equation

HRID 1257745 reaction equation
[C:1]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:15][CH:16]([CH3:19])[CH2:17]Br>C(C#N)(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:17][CH:16]([OH:15])[CH3:19])[CH2:11][CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 297401-Bromo-2-propanolHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 56973353tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamateYield 59%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(N-Boc-amino)-piperidine (1.0 g, 5.0 mmol), 2-hydroxybromopropane (1.0 g; 7.5 mmol) and TEA (0.76 g, 7.5 mmol) in AcCN (20 mL) was heated at 60° C. for 4 days. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried over Na2SO4 concentrated under reduced pressure. Purification of the residue by column chromatography on silica (0-5% 2M ammonia-MeOH in DCM) afforded [1-(2-hydroxy-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.76 g, 59%) as an oil. LCMS (Method G; ESI): RT=0.49 min, m+1=259.3.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography on silica (0-5% 2M ammonia-MeOH in DCM)

Sources & evidence

ORD record
ord-3e180069ac294000a1dfcc63fe2a63b2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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