(Diethylamino)sulfur trifluoride → HCID 57441094, compound

HRID 1435527Notes

Reaction equation

HRID 1435527 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:16][CH2:15][C:13](=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].CCN(S(F)(F)[F:23])CC>C1COCC1>[C:2]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:16][CH2:15][C:13]([F:23])=[CH:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 40424027tert-Butyl [(4-oxocyclohexyl)methyl]carbamate

Product 1

HCID 57441094HCID 57441094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-N-Boc-aminomethyl cyclohexanone (4.95 g, 21.8 mmol) was dissolved in THF (80 mL). DAST (4.3 mL, 32.7 mmol) was added dropwise and the solution was stirred at 50° C. for 5 h. The solvent was concentrated and the product purified by flash chromatography on silica gel using hexanes/EtOAc (3:1) as eluent. Yield: 1.62 g (30%). 1H NMR (400 MHz, CDCl3) δ 1.36-1.42 (m, 1 H), 1.44 (s, 9 H), 1.70-1.80 (m, 2 H), 1.82-1.90 (m, 1 H), 2.09-2.17 (m, 1 H), 2.17-2.29 (m, 2 H), 3.04-3.11 (m, 2 H), 4.61 (s, 1 H), 5.11-5.19 (m, 1 H).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe product purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-60854c32ad7c4d2fa5eee87cb92cf0e8
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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