Triethylamine → (S)-2-Amino-tert-butyldimethylsilyloxypropane

HRID 1808021Notes

Reaction equation

HRID 1808021 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:6]([Si:10]([CH3:12])([CH3:11])[O:4][CH2:3][CH:2]([NH2:1])[CH3:5])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 80307L-Alaninol

Product 1

HCID 21474737(S)-2-Amino-tert-butyldimethylsilyloxypropaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (S)-(+) 2-amino-1-propanol (1.04 g, 13.85 mmol), tert butyldimethylsilyl chloride (2.09 g, 13.85 mmol) and triethylamine (2 ml, 1.05 eq) was stirred in DCM overnight ca 16 h. The reaction was diluted with DCM, washed with water, satd. NH4Cl, brine, dried and evaporated to an oil. Silica gel purification of the crude using 3% MeOH/CH2Cl2 as eluent provided 2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethylamine (1.76 g, 80%); 1H NMR (300 MHz, CDCl3) 0.0 (s, 6H), 0.82 (s, 9H), 0.99 (d, J=6.5 Hz, 3H), 2.22 (bs, 2H), 2.98 (bs, 1H), 3.30 (dd, J=10 Hz, J=17.0 Hz, 1H), 3.48 (dd, J=10.0 Hz, J=4.3 Hz, 1H).

Workup

  1. washwashed with water
  2. dry with materialNH4Cl, brine, dried
  3. customevaporated to an oil
  4. customSilica gel purification of the crude

Sources & evidence

ORD record
ord-fae61425203747f380bd0ac483452202
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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