Ammonium Chloride → (s)-1-n-boc-pipecolamide

HRID 751650Notes

Reaction equation

HRID 751650 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C[N:18](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl-].[NH4+].CCN(C(C)C)C(C)C>CN(C=O)C>[C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C:14](=[O:16])[NH2:18])=[O:7])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 2756821(s)-1-n-boc-pipecolamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-Boc-L-pipecolinic acid (200 mg, 0.87 mmol) in DMF (3.5 mL) was added TBTU (336 mg, 1.05 mmol), ammonium chloride (93 mg, 1.74 mmol) then DIPEA (182 μL, 1.05 mmol) and the reaction stirred for 16 h. The mixture was partitioned between ethyl acetate (2×30 mL) and water (30 mL), and the organics combined before being washed with 1M sodium hydroxide (3×30 mL) and brine (3×30 mL). The organic solution was dried (MgSO4) and solvent removed in vacuo to give the title compound as a white solid. δH (d6 DMSO): 7.23 (1H, s), 6.97 (1H, s), 4.56–4.39 (1H, br m), 3.43–3.74 (1H, d), 3.14–2.90 (1H, br m), 2.09–2.00 (1H, d), 1.63–1.47 (3H, m), 1.30–1.17 (2H, m).

Workup

  1. customThe mixture was partitioned between ethyl acetate (2×30 mL) and water (30 mL)
  2. washbefore being washed with 1M sodium hydroxide (3×30 mL) and brine (3×30 mL)
  3. dry with materialThe organic solution was dried (MgSO4) and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-84074ee20d9f48b7b35b4c11a8e3d5b6
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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