Triethylamine → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 626122Notes

Reaction equation

HRID 626122 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (16 g, 85.4 mmol) and triethylamine (19 mL, 129 mmol) in 130 mL CH2Cl2 was added methanesulfonyl chloride (10 mL, 129 mmol) in 20 mL CH2Cl2 dropwise at 0° C. After addition, the reaction was stirred for 2.5 h at rt, then quenched with sat. NaHCO3 (aq.), and extracted with CH2Cl2. The extract was dried and concentrated to give the desired product (22.7 g, 100% yield) as a yellow solid.

Workup

  1. additionAfter addition
  2. customquenched with sat. NaHCO3 (aq.)
  3. extractionextracted with CH2Cl2
  4. customThe extract was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6cd3351e5fa44fa9c1a0afa4082279b
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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