Water → N-(tert-butoxycarbonyl)piperidine

HRID 1867975Notes

Reaction equation

HRID 1867975 reaction equation
NC1SC2C=C(OS(C3SC=CC=3)(=O)=O)C=CC=2N=1.[C:20]([N:27]1[CH2:35][CH2:34][CH:30](C(O)=O)[CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)C(C)C)(C)C.O>CN(C)C=O>[C:23]([O:22][C:20]([N:27]1[CH2:35][CH2:34][CH2:30][CH2:29][CH2:28]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 57980850HCID 57980850, compound2×

Product 1

HCID 7010304N-(tert-butoxycarbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1st step: A solution of thiophene-2-sulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 31) (80 mg, 0.256 mmol), Boc-isonipecotic acid (176 mg, 0.768 mmol) HBTU (291 mg, 0.768 mmol) and N,N-diisopropylethylamine (223 μl, 1.28 mmol) in 4 ml of dimethylformamide is stirred for 3 days at room temperature. 30 ml of water are added to the reaction medium, which is extracted with ethyl acetate. The organic phase is washed with water and with saturated sodium chloride solution, dried over magnesium sulfate and concentrated to dryness to give 4-[6-thiophene-2-sulfonyloxy)benzothiazol-2-ylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. extractionis extracted with ethyl acetate
  2. washThe organic phase is washed with water and with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-558304165ba049b68a2f2608dc5f92a4
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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