Triethylamine → (7S,9AS)-7-(((tert-butyldimethylsilyl)oxy)methyl)octahydropyrazino[2,1-c][1,4]oxazine

HRID 2074840Notes

Reaction equation

HRID 2074840 reaction equation
[CH2:1]1[C@@H:6]2[CH2:7][NH:8][C@H:9]([CH2:11][OH:12])[CH2:10][N:5]2[CH2:4][CH2:3][O:2]1.CCN(CC)CC.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[CH3:24][C:23]([Si:20]([CH3:22])([CH3:21])[O:12][CH2:11][C@@H:9]1[CH2:10][N:5]2[C@H:6]([CH2:1][O:2][CH2:3][CH2:4]2)[CH2:7][NH:8]1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 59215831((7S,9aS)-Octahydropyrazino[2,1-c][1,4]oxazin-7-yl)methanol

Product 1

HCID 59215768(7S,9AS)-7-(((tert-butyldimethylsilyl)oxy)methyl)octahydropyrazino[2,1-c][1,4]oxazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(7S,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-7-ylmethanol (D50, 680 mg, 3.95 mmol) was almost dissolved in dry DCM (12 mL) before adding Et3N (1.10 mL, 7.90 mmol), followed by TBDMS-Chloride (894 mg, 5.93 mmol). The resulting reaction mixture was stirred over the weekend at R.T., under argon. Left stirring for 2 more hours.

Workup

  1. customThe resulting reaction mixture
  2. waitLeft
  3. stirringstirring for 2 more hours

Sources & evidence

ORD record
ord-29d9d83589124690b3c4e91662b809c3
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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