Tert-Butylamine → HCID 11310321, compound

HRID 239732

Reaction equation

HRID 239732 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH3:6][CH:7]1[S:11](=[O:13])(=[O:12])[O:10][CH2:9][CH2:8]1>O1CCCC1>[C:1]([NH:5][CH2:9][CH2:8][CH:7]([S:11]([OH:13])(=[O:12])=[O:10])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxide

Product 1

HCID 11310321HCID 11310321, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butylamine (1.0 mL, 9.5 mmol) in tetrahydrofuran (15 mL) was added 2,4-butane sultone (1.33 g, 10.0 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid product was collected by filtration, washed with THF (2×20 mL), and dried in vacuo; affording compound ES: 1H NMR (DMSO, 500 MHz) 8 ppm 2.97 (t, 2H, J=6.6 Hz), 2.62 (m, 1H), 1.95 (m, 0.5H), 1.750 (m, 0.5H), 1.22 (s, 9H), 1.12 (d, 3H, J=6.8 Hz). 13C NMR (DMSO, 125 MHz) 8 ppm 56.17, 53.15, 29.87, 25.87, 17.05. ES-MS 207 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with THF (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bd12f7cd705c442bbe6b493bccc1905a
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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