Triethylamine → Tert-butyl 3-(tert-butyldimethylsilyloxy)-2-hydroxypropylcarbamate

HRID 2307820Notes

Reaction equation

HRID 2307820 reaction equation
[OH:1][CH:2]([CH2:12][OH:13])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:3][CH:2]([OH:1])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])([CH3:9])([CH3:10])[CH3:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 4206999tert-butyl N-(2,3-dihydroxypropyl)carbamate

Product 1

HCID 10881307Tert-butyl 3-(tert-butyldimethylsilyloxy)-2-hydroxypropylcarbamateYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of t-butyl N-(2,3-dihydroxypropyl)carbamate (9.0 g, 47 mmol) in CH2Cl2 (75 mL) was added t-butyldimethylsilyl chloride (7.80 g, 51.7 mmol), triethylamine (7.86 mL, 56.4 mmol) and DMAP (230 mg). The solution was stirred at rt overnight. After diluting with CH2Cl2 (50 mL), the solution was washed with water (2×100 mL), dried over MgSO4 and concentrated. The residual oil was distilled by Kugelrohr under vacuum to give the desired product (13.6 g, 95%). MS (DCI) m/z 306 (M+1)+.

Workup

  1. washthe solution was washed with water (2×100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. distillationThe residual oil was distilled by Kugelrohr under vacuum

Sources & evidence

ORD record
ord-9b20779b6592464faa5d90b4df2d6958
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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