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

HRID 237256Notes

Reaction equation

HRID 237256 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].CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH: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 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2.0 g, 10.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added Et3N (1.4 g, 1.9 mL, 13.4 mmol) and methanesulfonyl chloride (1.38 g, 0.94 mL, 12.1 mmol). After 1 h, brine was added and the mixture extracted with CH2Cl2 (2×). The combined organics were dried to give 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester that was used without further purification.

Workup

  1. extractionthe mixture extracted with CH2Cl2 (2×)
  2. customThe combined organics were dried

Sources & evidence

ORD record
ord-cbb165d4a0184d78b9db0915bcb7d501
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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