Dimethyl Sulfoxide → tert-Butyl N-(3-oxopropyl)carbamate

HRID 1846601Notes

Reaction equation

HRID 1846601 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 10910051tert-Butyl N-(3-oxopropyl)carbamateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3-hydroxy-propyl)-carbamic acid tert-butyl ester (3.0 g, 0.017 mol), N,N-diisopropylethylamine (7.31 mL, 0.042 mol), and dimethyl sulfoxide (1.84 mL, 0.026 mol) in dichloromethane (100 mL) was cooled to 0° C. and flushed with nitrogen. Sulfur trioxide-pyridine complex (6.68 g, 0.042 mol) was added under a stream of nitrogen and the reaction mixture was stirred for 2.5 h. The reaction mixture was quenched using 0.1 N HCl. The aqueous layer was discarded. The organic extract was washed with additional 0.1N HCl (2×) and brine(2×), dried with Na2SO4, filtered, and concentrated to dryness to provide the title compound (2.8 g) as a clear oil which was used without further purification. 1H NMR (DMSO, 400 mHz) δ (ppm): 9.57 (s, 1H), 6.81 (bs, 1H), 3.19-3.14 (m, 2H), 2.49-2.44 (m, 2H), 1.3 (s, 9H).

Workup

  1. customflushed with nitrogen
  2. additionSulfur trioxide-pyridine complex (6.68 g, 0.042 mol) was added under a stream of nitrogen
  3. customThe reaction mixture was quenched
  4. extractionThe organic extract
  5. washwas washed with additional 0.1N HCl (2×) and brine(2×)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ea51bfa3cf1d45158c191a6316c9e1b5
Source dataset
uspto-grants-2015_02
Patent number
US08952031B2

Reaction notes

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