Triethylamine → HCID 71713804, compound

HRID 2273856Notes

Reaction equation

HRID 2273856 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:29][C:30]([S:33](Cl)=[O:34])([CH3:32])[CH3:31].C(OCC)(=[O:38])C>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[S:33]([C:30]([CH3:32])([CH3:31])[CH3:29])(=[O:34])=[O:38])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[S:33]([C:30]([CH3:32])([CH3:31])[CH3:29])=[O:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 71580561HCID 71580561, compound

Product 2

HCID 71713804HCID 71713804, compoundHCID 89825291HCID 89825291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(6-((tert-butyldimethylsilyl)oxy)hexyl)cyclohexanamine (246 mg, 0.78 mmol) and triethyl amine (0.22 mL, 1.57 mmol) in methylene chloride (10 mL) at 0° C. was added 2-methylpropane-2-sulfinic chloride (0.13 mL, 1.01 mmol). The mixture was stirred for 2 hours before it was diluted with ethyl acetate and washed with saturated bicarbonate solution and brine. The organic phase was separated and concentrated. Purification on silica gel with ethyl acetate: hexanes from 0:1 to 3:7 provided desired compound, N-(6-((tert-butyldimethylsilyl)oxy)hexyl)-N-cyclohexyl-2-methylpropane-2-sulfinamide, as a clear oil (282.5 mg, 87%). 1H NMR (300 MHz, CDCl3): δ 3.55 (t, J=6.4 Hz, 2H), 3.14 (ddd, J=5.3, 11.7, 14.3 Hz, 1H), 2.94-2.76 (m, 1H), 2.64-2.46 (m, 1H), 2.04-1.92 (m, 2H), 1.84-1.64 (m, 3H), 1.64-1.38 (m, 7H), 1.38-0.94 (m, 6H), 1.14 (s, 9H), 0.85 (s, 9H), 0.05 (s, 6H).

Workup

  1. washwashed with saturated bicarbonate solution and brine
  2. customThe organic phase was separated
  3. concentrationconcentrated
  4. customPurification on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-186cdf8a42294457bea2b63cdd8e536d
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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