Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate → tert-Butyl 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidine-1-carboxylate

HRID 1035200Notes

Reaction equation

HRID 1035200 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.CS(O[CH:20]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21]1)(=O)=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[O:14][CH:20]1[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23]1

Participants

3

Reactant 2

HCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 580430903-Fluoro-4-(pyrrolidin-1-ylmethyl)phenol

Product 1

HCID 58043143tert-Butyl 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidine-1-carboxylateYield 80%

Procedure

Using a similar protocol as described in Example 29C employing 31A (6.6 g, 33.8 mmol) and tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (10.2 g, 40.6 mmol) as starting materials afforded 9.4 g (80%) of 31B as a solid. 1H NMR (500 MHz, CDCl3): δ 1.45 (s, 9H), 1.77 (m, 4H), 2.52 (m, 4H), 3.61 (s, 2H), 3.99 (m, 2H), 4.27 (m, 2H), 4.84 (m, 1H), 6.43 (dd, 1H), 6.49 (dd, 1H), 7.27 (t, 1H), MS (APCI+) m/z 351 [M+H]+.

Sources & evidence

ORD record
ord-9d85558092d14256b1ed5a99512f02cd
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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