Triethylamine → HCID 10881469, compound

HRID 1700953Notes

Reaction equation

HRID 1700953 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Si:13]([O:20][CH2:21][C@@H:22]([CH3:27])[CH2:23][CH2:24][CH2:25][OH:26])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>ClCCl.C(OCC)C>[CH3:8][S:9]([O:26][CH2:25][CH2:24][CH2:23][C@H:22]([CH3:27])[CH2:21][O:20][Si:13]([C:16]([CH3:18])([CH3:19])[CH3:17])([CH3:15])[CH3:14])(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14758908HCID 14758908, compound

Product 1

HCID 10881469HCID 10881469, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethyl amine (413 μl, 3.09 mmol, 1.53 equiv) and methanesulfonyl chloride (212 μl, 2.73 mmol, 1.35 equiv) is added to a solution of (S)-5-(tert-butyldimethylsilyloxy)-4-methyl-pentan-1-ol 6 (471 mg, 2.03 mmol) in 6.5 ml of dichloromethane. The mixture is stirred for 15 min at 0° C., diluted with diethyl ether (30 ml), washed with water (5 ml), 1.0 M hydrochloric acid (5 ml), saturated aqueous sodium bicarbonate solution (5 ml), and brine (5 ml). The organic phase is separated, dried over magnesium sulfate and concentrated in vacuo. (S)-1-methanesudonyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 7 (472 mg, 99%) is obtained as a colourless oil. 13C-NMR (100 MHz, CDCl3): δ=70.44; 67.98; 37.41; 35.31; 28.99; 26.80; 25.95; 18.34; 16.56; −5.37, −5.38 (—SiMe2tBu).

Workup

  1. washwashed with water (5 ml), 1.0 M hydrochloric acid (5 ml), saturated aqueous sodium bicarbonate solution (5 ml), and brine (5 ml)
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4028fec1d602496d80cfca0d1632f300
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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