Acetic Acid → tert-Butyl 4-[(prop-2-en-1-yl)amino]piperidine-1-carboxylate

HRID 2185573Notes

Reaction equation

HRID 2185573 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(O)(=O)C.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:4][CH2:1][CH:2]=[CH2:3])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7853AllylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18677683tert-Butyl 4-[(prop-2-en-1-yl)amino]piperidine-1-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Allylamine (0.45 mL, 0.34 g, 6.0 mmol), acetic acid (0.300 mL, 315 mg, 5.24 mmol), and 3 Å molecular sieves (2.00 g) were added to a solution of 1-(t-butyoxycarbonyl)-4-piperidone (1.00 g, 5.01 mmol) in 1,2-dichloroethane (14 mL). The resulting mixture was stirred for 30 min at rt, then treated with sodium triacetoxyborohydride (1.62 g, 7.6 mmol). The reaction was stirred at rt for 3 h, then partitioned between EtOAc (30 mL) and sat'd NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (30 mL) and the organic layers were washed with 20 mL of sat'd NaCl, combined, dried over Na2SO4, and evaporated to give 1.20 g of crude 1-(t-butoxycarbonyl)-4-(N-prop-2-enyl)aminopiperidine.

Workup

  1. stirringThe reaction was stirred at rt for 3 h
  2. custompartitioned between EtOAc (30 mL) and sat'd NaHCO3 (20 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (30 mL)
  4. washthe organic layers were washed with 20 mL of sat'd NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-4b12b401723c427ca265570e3e43293a
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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