Triethylsilane → (3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl ester

HRID 1169237Notes

Reaction equation

HRID 1169237 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][CH2:8][O:9][CH2:10][C:11]=1[NH:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:5])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:7][CH2:8][O:9][CH2:10][C@H:11]1[NH:12][C@@H:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 59042158(R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester

Product 1

HCID 59042167(3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl esterYield 36%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of crude (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester (4.53 g, ca. 16.5 mmol) was dissolved in trifluoroacetic acid (45 mL) and treated with triethylsilane (7.9 mL, 49.4 mmol). The mixture was stirred for 17 h and then concentrated. The residue was dissolved in water and adjusted to pH 10 with 50% sodium hydroxide. The mixture was extracted with dichloromethane, and the combined organic phases were dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (40% diethyl ether/petroleum ether) to provide the product as a colorless oil (1.63 g, 36%). 1H NMR (300 mHz, CDCl3) δ7.22 (m, 4H), 7.16 (m, 1H), 4.14 (q, J=7.3 Hz, 2H), 3.77 (m, 2H), 3.60 (q, J=7.3 Hz, 1H), 3.23 (m, 1H), 2.83 (m, 2H), 2.31 (m, 1H), 1.77 (m, 2H), 1.24 (m, 6H), ESI MS: (M+H)+=278.1 (100%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (40% diethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-7bcf9401f0f743fca07f760c4d7c9db0
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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