Triethylamine → [4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amine

HRID 230812Notes

Reaction equation

HRID 230812 reaction equation
[Si:1]([O:8][CH:9]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:30]=[CH:29][C:26]([CH:27]=O)=[C:25]([CH3:31])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.Cl.[NH2:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:50])=[O:49]>CO.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[Si:1]([O:8][CH:9]([C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][NH:45][CH2:46][CH2:47][S:48]([CH3:51])(=[O:50])=[O:49])=[C:25]([CH3:31])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:32])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 866047794-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzaldehyde

Product 1

HCID 68464086[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amineYield 51%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzaldehyde (2.40 g, 4.71 mmol), Et3N (0.9 ml, 6.12 mmol), and 2-aminoethylmethylsulfone hydrochloride (0.78 g, 5.18 mmol) is treated with Ti(OiPr)4 (1.8 ml, 6.12 mmol). The mixture is stirred for 1 h, diluted with CH3OH (20 mL), then NaBCNH3 (0.33 g, 5.18 mmol) is added. The mixture is stirred overnight, quenched with H2O (3 mL), stirred for 1 h., and filtered through SiO2 with EtOAc (100 mL) wash. The filtrate is concentrated and chromatographed (75-80% EtOAc) to give the title compound (1.47 g, 2.38 mmol, 51%).

Workup

  1. additionNaBCNH3 (0.33 g, 5.18 mmol) is added
  2. stirringThe mixture is stirred overnight
  3. customquenched with H2O (3 mL)
  4. stirringstirred for 1 h.
  5. filtrationfiltered through SiO2 with EtOAc (100 mL)
  6. washwash
  7. concentrationThe filtrate is concentrated
  8. customchromatographed (75-80% EtOAc)

Sources & evidence

ORD record
ord-afc8005e304f48a3abf11a266437bb6c
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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