Triethylamine → (S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

HRID 1926313Notes

Reaction equation

HRID 1926313 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (0.750 g, 4.00 mmol) in DCM (10 mL) was cooled to 0° C. and charged with triethylamine (0.67 mL, 4.8 mmol), methanesulfonyl chloride (0.34 mL, 4.4 mmol), and 4-dimethylaminopyridine (0.005 g, 0.04 mmol) and stirred at ambient temperature for 6 h. The reaction mixture was partitioned between CHCl3 and sat. NaHCO3 and separated. The aqueous layer was re-extracted with CHCl3 (3×) and the combined organic fractions were washed with sat. NaHCO3 (2×), brine (2×), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a pale yellow oil. This material was taken on to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=1.47 (s, 9H), 2.05-2.36 (m, 2H), 3.05 (s, 3H), 3.43-3.74 (m, 4H), 5.24-5.30 (m, 1H).

Workup

  1. customThe reaction mixture was partitioned between CHCl3 and sat. NaHCO3
  2. customseparated
  3. extractionThe aqueous layer was re-extracted with CHCl3 (3×)
  4. washthe combined organic fractions were washed with sat. NaHCO3 (2×), brine (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa8efc476486484694259d3973edbbcb
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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