Triethylamine → (S)-3-(tert-Butyldimethylsilanyloxy)-1-phenylpropylamine

HRID 339823Notes

Reaction equation

HRID 339823 reaction equation
Cl.[NH2:2][C@H:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21]>ClCCl>[Si:24]([O:6][CH2:5][CH2:4][C@H:3]([NH2:2])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 50998248(S)-3-Amino-3-phenylpropan-1-ol hydrochloride

Product 1

HCID 68287924(S)-3-(tert-Butyldimethylsilanyloxy)-1-phenylpropylamineYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.50 g of (S)-3-amino-3-phenylpropan-1-ol hydrochloride were initially charged in 20 ml of dichloromethane and then 2.77 ml of triethylamine and 1.30 g of tert-butyldimethylchlorosilane were added. After stirring at room temperature for 3 hours, the reaction solution was extracted three times with 30 ml of water, dried by means of a phase separator cartridge (Chromabond® PTS), concentrated by rotary evaporation and dried under high vacuum. This gave the product (2.06 g) with a molecular weight of 265.5 g/mol (C15H27NOSi); MS (ESI): m/e=266 (M+H+).

Workup

  1. extractionthe reaction solution was extracted three times with 30 ml of water
  2. customdried by means of a phase separator cartridge (Chromabond® PTS)
  3. concentrationconcentrated by rotary evaporation
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-19276d59e56f438eaae8c0b53c5afa25
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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