(Diethylamino)sulfur trifluoride → HCID 68291692, compound

HRID 1507922Notes

Reaction equation

HRID 1507922 reaction equation
CCN(S(F)(F)[F:7])CC.[CH2:10]([N:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:18]([C:20]1(O)[CH2:22][CH2:21]1)[CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[CH2:10]([N:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:18]([C:20]1([F:7])[CH2:22][CH2:21]1)[CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 68349488HCID 68349488, compound

Product 1

HCID 68291692HCID 68291692, compoundYield 21.73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (2.99 ml, 22.60 mmol) was added dropwise to a stirred solution of (R)-1-(1-(dibenzylamino)ethyl)cyclopropanol (5.3 g, 18.83 mmol) in dichloromethane (94 ml) at −78° C. under a nitrogen atmosphere. The reaction was allowed to stir for about 2 hrs before quenching with sat. sodium bicarbonate solution (100 mL) via dropwise addition. The quenched reaction was allowed to warm slowly to rt overnight. The organic layer was separated, dried (MgSO4) and evaporated in vacuo before purifying by column chromatography using hexane to 2% ethyl acetate in hexane as eluent to give the title compound (1.16 g, 4.09 mmol, 21.73% yield). HPLC (condition B): retention time=3.69 min. LCMS (condition B): m/z 284.2. 1H NMR (400 MHz, MeOD) δ ppm 7.11-7.52 (10 H, m), 4.98-5.32 (1 H, m), 3.76-4.08 (4 H, m), 1.08-1.42 (3 H, m), 0.47-0.82 (4 H, m).

Workup

  1. custombefore quenching with sat. sodium bicarbonate solution (100 mL) via dropwise addition
  2. customThe quenched reaction
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. custombefore purifying by column chromatography

Sources & evidence

ORD record
ord-8c97d039614d4f95ae7fc5f56c680fbd
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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