Ethanolamine → tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

HRID 1888077Notes

Reaction equation

HRID 1888077 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1([F:26])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(CN)O>>[NH2:3][CH2:12][C:13]1([F:26])[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 53415317Tert-butyl 4-((1,3-dioxoisoindolin-2-yl)methyl)-4-fluoropiperidine-1-carboxylate

Product 1

HCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

Conditions

Temperature
60 °C

Procedure

A mixture of 3-3 (11.0 g) and 25 mL ethanolamine was stirred at 60° C. for 1 h. The reaction was then allowed to cool to room temperature, poured into ice-water (100 mL), and extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine (150 mL), dried over MgSO4, filtered, and concentrated in vacuo, giving 5.82 g of crude 3-4 as a viscous amber oil. 1H NMR (CDCl3, 300 MHz): 3.94 (br, 2H), 3.08 (m, 2H), 1.85 (m, 2H), 1.51 (m, 4H), 1.44 (s, 9H); MS (Electrospray): m/z 218.2 (M−Me+H), 177.2 (M−t−Bu+H).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. washThe combined organic layers were washed with brine (150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3aff64ee755c4a5faffbcb56488be7ee
Source dataset
uspto-grants-2013_08
Patent number
US08501773B2

Reaction notes

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