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

HRID 1850081Notes

Reaction equation

HRID 1850081 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (1.21 g, 6.99 mmol) and Et3N (0.85 g, 1.2 mL, 8.4 mmol) in CH2Cl2 (35 mL) at 0° C. was added methanesulfonyl chloride (0.88 g, 0.60 mL, 7.7 mmol). After 1 h, brine was added and the reaction extracted with CH2Cl2 (2×). The combined organics were dried to give 1.65 g (94%) of 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester a yellow solid that was used without further purification. 1H NMR (CDCl3): 5.20 (tt, J=6.7, 4.2 Hz, 1H), 4.28 (ddd, J=10.3, 6.7, 1.2 Hz, 2H), 4.10 (ddd, J=10.4, 4.2, 1.1 Hz, 2H), 3.07 (s, 3H), 1.44 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-eda23930612842949d4116dcb477b06c
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

Loading…