Triethylamine → N-[1-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxypropyl]heptanamide

HRID 1781346Notes

Reaction equation

HRID 1781346 reaction equation
[OH:1][CH:2]([CH3:15])[CH:3]([NH:6][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:4][OH:5].[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[CH3:20][C:19]([Si:16]([CH3:18])([CH3:17])[O:5][CH2:4][CH:3]([NH:6][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:2]([OH:1])[CH3:15])([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 76480420N-[2-Hydroxy-1-(hydroxymethyl)propyl]heptanamide

Product 1

HCID 76412708N-[1-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxypropyl]heptanamideYield 109.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 11c, (1.945 g) of t-butyldimethylsilyl chloride, (1.4165 g) of triethylamine (951 mg, 1.31 mL), and 4-dimethylaminopyridine (42.76 mg) in 13 mL of methylene chloride is stirred under argon at room temperature for 18 h. The reaction mixture is diluted with methylene chloride and water added. The organic layer is separated, washed with water, dried and evaporated to give 3.25 g of a residual oil which is purified by chromatography by elution with 1:5 ethyl acetate/hexane to give 2.30 g of the desired product as an oil. NMR δ 0.08 (d, 6 H), 0.89 (t, 3 H), 0.90 (s, 9 H), 1.16 (d, 3 H), 1.65 (m, 2 H), 2.24 (t, 2 H), 3.47 (s, 1 H), 3.84 (m, 1 H), 3.85 (s, 2 H), 4.28 (q, 1 H), 6.13 (brd, 1 H); MS (FAB) m/z=332 (M+H calc'd for C17H38NO3Si 332).

Workup

  1. additionadded
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-160aa4a07a0a4c1883d138198c5f37bd
Source dataset
uspto-grants-1997_05
Patent number
US05633280

Reaction notes

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