Hydrochloric Acid → (2S)-2-amino-3-{3-[(trimethylsilyl)ethynyl]phenyl}propan-1-ol

HRID 339977Notes

Reaction equation

HRID 339977 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:17]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=1.CO.Cl.O1CCOCC1>>[NH2:17][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][Si:13]([CH3:15])([CH3:14])[CH3:16])[CH:6]=1)[CH2:2][OH:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 86681467tert-butyl ((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)carbamate

Product 1

HCID 86681469(2S)-2-amino-3-{3-[(trimethylsilyl)ethynyl]phenyl}propan-1-olYield 102.7%

Procedure

tert-Butyl ((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)carbamate (0.84 g, 2.4 mmol), methanol (2.0 mL, 49 mmol), and 4.0 M hydrogen chloride in dioxane (5.0 mL, 20 mmol) were mixed together and stirred at room temperature for 1 h. The solvent was removed under vacuum to give 0.61 g (98% yield) of the desired product. LC-MS found: 248.0 (m+1).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-78fe68ece2bf4524acf71f2880b8b88f
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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