Triethylamine → (2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidine

HRID 553027Notes

Reaction equation

HRID 553027 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11074142(R)-1-Boc-2-azetidinemethanol

Product 1

HCID 11140030(2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidineYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (2R)-1-Boc-2-(hydroxymethyl)azetidine (1.5 g, 8.0 mmol; see Tetrahedron Asym. 1998, 9, 2791) and triethylamine (3.5 g, 35 mmol; Spectrum) in dry THF (20 mL) was cooled to 0° C., and methanesulfonyl chloride (0.75 mL, 9.7 mmol; Aldrich) was added slowly with stirring. The reaction mixture was allowed to warm to room temperature and stir for 1 hour, then the solid was removed by filtration and the organic phase was concentrated. The residue was dissolved in dichloromethane (40 mL), washed with water (20 mL), and then concentrated to afford the title compound (800 mg. 3.0 mmol; 38% yield). MS (DCI/NH3): 266 (M+1)+, 283 (M+18)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir for 1 hour
  3. customthe solid was removed by filtration
  4. concentrationthe organic phase was concentrated
  5. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with water (20 mL)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d81b9abca4d148baa99c807c01aa2f6e
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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