Triethylamine → HCID 86673831, compound

HRID 1527380Notes

Reaction equation

HRID 1527380 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][S:17]([CH3:16])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67092752tert-butyl (2S,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86673831HCID 86673831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2S,4R)-4-Fluoro-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2.87 g, 13.1 mmol) was dissolved in 45 mL of CH2Cl2. The mixture was cooled down to 0° C., and methanesulfonyl chloride (2.55 mL, 32.8 mmol) and triethylamine (4.56 mL, 32.8 mmol) were added. The mixture was allowed to warm to RT and stirred for 1.5 h. The mixture was quenched with a saturated aqueous solution of NaHCO3, extracted twice with CH2Cl2, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAC 3:7) to afford the desired material. TLC, Rf (c-hexane/EtOAc 1:1)=0.4; MS: 320.0 [M+Na]+, 198.1 [MH−Boc]+, 617.2 [2M+Na]+.

Workup

  1. temperatureto warm to RT
  2. customThe mixture was quenched with a saturated aqueous solution of NaHCO3
  3. extractionextracted twice with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAC 3:7)

Sources & evidence

ORD record
ord-4e5d448bbf7a435a8219ea5a0cd14a3e
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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