Reaction #1726687

Reaction equation

K2CO3

TFA

3A

tert-Butyl 3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidine-1-carboxylate

K2CO3

→

3B

Yield 94.6%

6-(4-(Azetidin-3-yloxy)benzyl)-2-oxa-6-azaspiro[3.3]heptane

Yield 94.6%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 20 min
2. 2
   Otherthe mixture was transferred to a separatory funnel
3. 3
   OtherThe layers were separated
4. 4
   OtherThe combined organic solutions were dried (phase separator)
5. 5
   Otherevaporated

Procedure

3A (0.19 g, 0.52 mmol) was dissolved in dichloromethane (20 mL) and TFA (1.95 mL, 26 mmol) was added. The reaction mixture was stirred at room temperature for two hours. K2CO3 (5 g) was added in portions and the mixture was stirred for 20 min. A saturated solution of K2CO3 (aq) was added and the mixture was transferred to a separatory funnel. The layers were separated and the aqueous layer was further extracted several times with dichloromethane. The combined organic solutions were dried (phase separator) and evaporated. There was obtained 128 mg (94%) of 3B as an oil. 1H NMR (500 MHz, CDCl3): δ 3.34 (s, 4H), 3.45 (s, 2H), 3.80 (m, 2H), 3.92 (m, 2H), 4.72 (s, 4H), 4.98 (m, 1H), 6.69 (d, 2H), 7.13 (d, 2H), MS (APCI+) m/z 261 [M+H]+.

Source